Product Name

  • Name

    1,3-Dibromo-5-fluoro-2-iodobenzene

  • EINECS
  • CAS No. 62720-29-0
  • Article Data1
  • CAS DataBase
  • Density 2.564 g/cm3
  • Solubility
  • Melting Point 134-137 °C
  • Formula C6H2Br2FI
  • Boiling Point 292.8 °C at 760 mmHg
  • Molecular Weight 379.793
  • Flash Point 130.9 °C
  • Transport Information
  • Appearance beige to pinkish or pale brown
  • Safety 24/25
  • Risk Codes 36/37/38
  • Molecular Structure Molecular Structure of 62720-29-0 (1,3-Dibromo-5-fluoro-2-iodobenzene)
  • Hazard Symbols IrritantXi
  • Synonyms 1,3-Dibromo-5-fluoro-2-iodobenzene;
  • PSA 0.00000
  • LogP 3.95530

Synthetic route

C10H12Br2FN3
401631-93-4

C10H12Br2FN3

1,3-dibromo-2-iodo-5-fluorobenzene
62720-29-0

1,3-dibromo-2-iodo-5-fluorobenzene

Conditions
ConditionsYield
With hydrogen iodide In acetonitrile at 60℃; for 1.5h;71%
2,6-dibromo-4-fluoroaniline
344-18-3

2,6-dibromo-4-fluoroaniline

1,3-dibromo-2-iodo-5-fluorobenzene
62720-29-0

1,3-dibromo-2-iodo-5-fluorobenzene

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 98 percent / i-pentyl nitrite; HOAc / 0 - 5 °C
2: 95 percent / aq. NaOH / 0.5 h / 0 - 5 °C
3: 71 percent / aq. HI / acetonitrile / 1.5 h / 60 °C
View Scheme
2,6-dibromo-4-fluorobenzenediazonium o-benzenedisulfonimide

2,6-dibromo-4-fluorobenzenediazonium o-benzenedisulfonimide

1,3-dibromo-2-iodo-5-fluorobenzene
62720-29-0

1,3-dibromo-2-iodo-5-fluorobenzene

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 95 percent / aq. NaOH / 0.5 h / 0 - 5 °C
2: 71 percent / aq. HI / acetonitrile / 1.5 h / 60 °C
View Scheme
1,3-dibromo-2-iodo-5-fluorobenzene
62720-29-0

1,3-dibromo-2-iodo-5-fluorobenzene

prenyl bromide
870-63-3

prenyl bromide

1,3-dibromo-5-fluoro-2-(3-methylbut-2-enyl)benzene

1,3-dibromo-5-fluoro-2-(3-methylbut-2-enyl)benzene

Conditions
ConditionsYield
Stage #1: 1,3-dibromo-5-fluoro-2-iodobenzene With isopropylmagnesium chloride In tetrahydrofuran at -20 - 0℃; for 1h; Inert atmosphere;
Stage #2: prenyl bromide With copper(l) iodide In tetrahydrofuran at 0 - 20℃;		85%
1,3-dibromo-2-iodo-5-fluorobenzene
62720-29-0

1,3-dibromo-2-iodo-5-fluorobenzene

thioacetic acid S-(2-acetylamino-phenyl)ester
1204-55-3

thioacetic acid S-(2-acetylamino-phenyl)ester

4-bromo-2-fluoro-10H-phenothiazine

4-bromo-2-fluoro-10H-phenothiazine

Conditions
ConditionsYield
With caesium carbonate In N,N-dimethyl-formamide at 130℃; for 10h; Inert atmosphere;65%
1,3-dibromo-2-iodo-5-fluorobenzene
62720-29-0

1,3-dibromo-2-iodo-5-fluorobenzene

phenylboronic acid
98-80-6

phenylboronic acid

2,6-dibromo-4-fluorobiphenyl
1383568-74-8

2,6-dibromo-4-fluorobiphenyl

Conditions
ConditionsYield
Stage #1: 1,3-dibromo-5-fluoro-2-iodobenzene With [1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene](3-chloropyridyl)palladium(II) dichloride; potassium carbonate In 1,4-dioxane at 20℃; for 1h; Suzuki-Miyaura coupling; Inert atmosphere;
Stage #2: phenylboronic acid In 1,4-dioxane for 36h; Suzuki-Miyaura coupling; Inert atmosphere; Reflux;		58%
1,3-dibromo-2-iodo-5-fluorobenzene
62720-29-0

1,3-dibromo-2-iodo-5-fluorobenzene

N,N-dimethyl-formamide
68-12-2, 33513-42-7

N,N-dimethyl-formamide

2,6-dibromo-4-fluorobenzaldehyde
938467-02-8

2,6-dibromo-4-fluorobenzaldehyde

Conditions
ConditionsYield
Stage #1: 1,3-dibromo-5-fluoro-2-iodobenzene With isopropylmagnesium chloride In diethyl ether; toluene at -35 - -25℃; for 2h;
Stage #2: N,N-dimethyl-formamide In diethyl ether; toluene at -19 - 10℃; for 2h; Product distribution / selectivity;		54%
Stage #1: 1,3-dibromo-5-fluoro-2-iodobenzene With isopropylmagnesium chloride In diethyl ether; toluene at -35 - -25℃; for 2h;
Stage #2: N,N-dimethyl-formamide In diethyl ether; toluene at -19 - 10℃; for 2h;		54%
Stage #1: 1,3-dibromo-5-fluoro-2-iodobenzene With isopropylmagnesium chloride In ethyl acetate; toluene at -35 - -25℃; for 2h;
Stage #2: N,N-dimethyl-formamide In ethyl acetate; toluene at 10 - 20℃; for 3h;		54%
Stage #1: 1,3-dibromo-5-fluoro-2-iodobenzene With isopropylmagnesium chloride In diethyl ether; toluene at -35 - -25℃; for 1.5h;
Stage #2: N,N-dimethyl-formamide In diethyl ether; toluene at -19 - 10℃; for 1.5h;		54%
Stage #1: 1,3-dibromo-5-fluoro-2-iodobenzene With isopropylmagnesium chloride In tetrahydrofuran; toluene at -35 - -25℃; for 2h;
Stage #2: N,N-dimethyl-formamide In tetrahydrofuran; toluene at -35 - 20℃; for 1.5h;		49%
1,3-dibromo-2-iodo-5-fluorobenzene
62720-29-0

1,3-dibromo-2-iodo-5-fluorobenzene

isopropylmagnesium chloride
1068-55-9

isopropylmagnesium chloride

N,N-dimethyl-formamide
68-12-2, 33513-42-7

N,N-dimethyl-formamide

2,6-dibromo-4-fluorobenzaldehyde
938467-02-8

2,6-dibromo-4-fluorobenzaldehyde

Conditions
ConditionsYield
Stage #1: 1,3-dibromo-5-fluoro-2-iodobenzene; isopropylmagnesium chloride In diethyl ether; toluene at -35 - -25℃; for 2h;
Stage #2: N,N-dimethyl-formamide In diethyl ether; toluene at -19 - 10℃; for 3h;		54%
...Expand
1,3-dibromo-2-iodo-5-fluorobenzene
62720-29-0

1,3-dibromo-2-iodo-5-fluorobenzene

1,3-dibromo-5-fluorobenzene
1435-51-4

1,3-dibromo-5-fluorobenzene

Conditions
ConditionsYield
With isopropylmagnesium chloride In tetrahydrofuran; toluene at -35 - -25℃; for 2h; Inert atmosphere;
1,3-dibromo-2-iodo-5-fluorobenzene
62720-29-0

1,3-dibromo-2-iodo-5-fluorobenzene

N,N-dimethyl-formamide
68-12-2, 33513-42-7

N,N-dimethyl-formamide

A

2,6-dibromo-4-fluorobenzaldehyde
938467-02-8

2,6-dibromo-4-fluorobenzaldehyde

B

1,3-dibromo-5-fluorobenzene
1435-51-4

1,3-dibromo-5-fluorobenzene

Conditions
ConditionsYield
Stage #1: 1,3-dibromo-5-fluoro-2-iodobenzene With isopropylmagnesium chloride In tetrahydrofuran Inert atmosphere;
Stage #2: N,N-dimethyl-formamide In tetrahydrofuran; water Inert atmosphere;
...Expand
1,3-dibromo-2-iodo-5-fluorobenzene
62720-29-0

1,3-dibromo-2-iodo-5-fluorobenzene

2-(7,7-dimethyl-1-oxo-3,4,7,8-tetrahydro-1H-cyclopenta[4,5]pyrrolo[1,2-a]pyrazin-2(6H)-yl)-4-fluoro-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzyl acetate
1346675-25-9

2-(7,7-dimethyl-1-oxo-3,4,7,8-tetrahydro-1H-cyclopenta[4,5]pyrrolo[1,2-a]pyrazin-2(6H)-yl)-4-fluoro-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzyl acetate

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1.1: isopropylmagnesium chloride / toluene; ethyl acetate / 2 h / -35 - -25 °C
1.2: 3 h / 10 - 20 °C
2.1: sodium tetrahydroborate; ethanol / 4 h / 10 °C
3.1: triethylamine / dichloromethane / 16 h / 20 °C
4.1: caesium carbonate / 1,4-dioxane / 0.5 h / Sealed tube
4.2: 16 h / 100 °C
5.1: potassium acetate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 / dichloromethane; 1,4-dioxane / 5 h / 100 °C
View Scheme
Multi-step reaction with 5 steps
1.1: isopropylmagnesium chloride / toluene; ethyl acetate / 2 h / -35 - -25 °C
1.2: 3 h / 10 - 20 °C
2.1: sodium tetrahydroborate; ethanol / 4 h / 10 °C
3.1: pyridine / dichloromethane / 5 h / 0 - 20 °C
4.1: caesium carbonate / 1,4-dioxane / 0.5 h / Sealed tube
4.2: 16 h / 100 °C
5.1: potassium acetate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 / dichloromethane; 1,4-dioxane / 5 h / 100 °C
View Scheme
1,3-dibromo-2-iodo-5-fluorobenzene
62720-29-0

1,3-dibromo-2-iodo-5-fluorobenzene

(2,6-dibromo-4-fluorophenyl)methanol
1346674-69-8

(2,6-dibromo-4-fluorophenyl)methanol

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: isopropylmagnesium chloride / toluene; ethyl acetate / 2 h / -35 - -25 °C
1.2: 3 h / 10 - 20 °C
2.1: sodium tetrahydroborate; ethanol / 4 h / 10 °C
View Scheme
Multi-step reaction with 3 steps
1: hydrogenchloride / toluene; diethyl ether / 2 h / -35 - -25 °C
2: toluene; diethyl ether / 3 h / -25 - 10 °C
3: sodium tetrahydroborate / ethanol / 4 h / 10 °C
View Scheme
Multi-step reaction with 2 steps
1.1: diethyl ether; toluene / 2 h / -35 - -25 °C
1.2: 3 h / -19 - 10 °C
2.1: sodium tetrahydroborate / ethanol / 4 h / 10 °C
View Scheme
1,3-dibromo-2-iodo-5-fluorobenzene
62720-29-0

1,3-dibromo-2-iodo-5-fluorobenzene

2-bromo-4-fluoro-6-(1-oxo-3,4,6,7,8,9-hexahydropyrazino[1,2-a]indol-2(1H)-yl)benzyl acetate
1346673-13-9

2-bromo-4-fluoro-6-(1-oxo-3,4,6,7,8,9-hexahydropyrazino[1,2-a]indol-2(1H)-yl)benzyl acetate

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1.1: isopropylmagnesium chloride / toluene; ethyl acetate / 2 h / -35 - -25 °C
1.2: 3 h / 10 - 20 °C
2.1: sodium tetrahydroborate; ethanol / 4 h / 10 °C
3.1: triethylamine / dichloromethane / 16 h / 20 °C
4.1: tris-(dibenzylideneacetone)dipalladium(0); 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene; caesium carbonate / 1,4-dioxane / 16 h / 100 °C / Inert atmosphere
View Scheme
Multi-step reaction with 4 steps
1.1: isopropylmagnesium chloride / toluene; ethyl acetate / 2 h / -35 - -25 °C
1.2: 3 h / 10 - 20 °C
2.1: sodium tetrahydroborate; ethanol / 4 h / 10 °C
3.1: pyridine / dichloromethane / 5 h / 0 - 20 °C
4.1: tris-(dibenzylideneacetone)dipalladium(0); 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene; caesium carbonate / 1,4-dioxane / 16 h / 100 °C / Inert atmosphere
View Scheme
Multi-step reaction with 5 steps
1: hydrogenchloride / toluene; diethyl ether / 2 h / -35 - -25 °C
2: toluene; diethyl ether / 3 h / -25 - 10 °C
3: sodium tetrahydroborate / ethanol / 4 h / 10 °C
4: pyridine / dichloromethane / 5 h / 0 - 20 °C
5: tris-(dibenzylideneacetone)dipalladium(0); 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene; caesium carbonate / 1,4-dioxane / 16 h / 100 °C / Inert atmosphere
View Scheme
Multi-step reaction with 4 steps
1.1: diethyl ether; toluene / 2 h / -35 - -25 °C
1.2: 3 h / -19 - 10 °C
2.1: sodium tetrahydroborate / ethanol / 4 h / 10 °C
3.1: triethylamine / dichloromethane / 16 h / 10 °C / Inert atmosphere
4.1: tris-(dibenzylideneacetone)dipalladium(0); 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene; caesium carbonate / 1,4-dioxane / 16 h / 100 °C / Inert atmosphere
View Scheme
1,3-dibromo-2-iodo-5-fluorobenzene
62720-29-0

1,3-dibromo-2-iodo-5-fluorobenzene

4-Fluoro-2-(1-oxo-3,4,6,7,8,9-hexahydro-pyrazino[1,2-a]indol-2(1H)-yl)-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzyl acetate
1346673-38-8

4-Fluoro-2-(1-oxo-3,4,6,7,8,9-hexahydro-pyrazino[1,2-a]indol-2(1H)-yl)-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzyl acetate

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1.1: isopropylmagnesium chloride / toluene; ethyl acetate / 2 h / -35 - -25 °C
1.2: 3 h / 10 - 20 °C
2.1: sodium tetrahydroborate; ethanol / 4 h / 10 °C
3.1: triethylamine / dichloromethane / 16 h / 20 °C
4.1: tris-(dibenzylideneacetone)dipalladium(0); 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene; caesium carbonate / 1,4-dioxane / 16 h / 100 °C / Inert atmosphere
5.1: potassium acetate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / 1,4-dioxane / 15 h / 100 °C / Inert atmosphere
View Scheme
Multi-step reaction with 5 steps
1.1: isopropylmagnesium chloride / toluene; ethyl acetate / 2 h / -35 - -25 °C
1.2: 3 h / 10 - 20 °C
2.1: sodium tetrahydroborate; ethanol / 4 h / 10 °C
3.1: pyridine / dichloromethane / 5 h / 0 - 20 °C
4.1: tris-(dibenzylideneacetone)dipalladium(0); 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene; caesium carbonate / 1,4-dioxane / 16 h / 100 °C / Inert atmosphere
5.1: potassium acetate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / 1,4-dioxane / 15 h / 100 °C / Inert atmosphere
View Scheme
Multi-step reaction with 6 steps
1: hydrogenchloride / toluene; diethyl ether / 2 h / -35 - -25 °C
2: toluene; diethyl ether / 3 h / -25 - 10 °C
3: sodium tetrahydroborate / ethanol / 4 h / 10 °C
4: pyridine / dichloromethane / 5 h / 0 - 20 °C
5: tris-(dibenzylideneacetone)dipalladium(0); 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene; caesium carbonate / 1,4-dioxane / 16 h / 100 °C / Inert atmosphere
6: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate / 1,4-dioxane / 15 h / 100 °C / Inert atmosphere
View Scheme
Multi-step reaction with 5 steps
1.1: diethyl ether; toluene / 2 h / -35 - -25 °C
1.2: 3 h / -19 - 10 °C
2.1: sodium tetrahydroborate / ethanol / 4 h / 10 °C
3.1: triethylamine / dichloromethane / 16 h / 10 °C / Inert atmosphere
4.1: tris-(dibenzylideneacetone)dipalladium(0); 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene; caesium carbonate / 1,4-dioxane / 16 h / 100 °C / Inert atmosphere
5.1: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate / 1,4-dioxane / 15 h / 100 °C / Inert atmosphere
View Scheme
1,3-dibromo-2-iodo-5-fluorobenzene
62720-29-0

1,3-dibromo-2-iodo-5-fluorobenzene

(S)-2-(5-(5-(2-ethyl-4-(oxetan-3-yl)piperazin-1-yl)pyridin-2-ylamino)-1-methyl-6-oxo-1,6-dihydropyridin-3-yl)-4-fluoro-6-(1-oxo-3,4,6,7,8,9-hexahydropyrazino[1,2-a]indol-2(1H)-yl)benzyl acetate
1433989-74-2

(S)-2-(5-(5-(2-ethyl-4-(oxetan-3-yl)piperazin-1-yl)pyridin-2-ylamino)-1-methyl-6-oxo-1,6-dihydropyridin-3-yl)-4-fluoro-6-(1-oxo-3,4,6,7,8,9-hexahydropyrazino[1,2-a]indol-2(1H)-yl)benzyl acetate

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1.1: isopropylmagnesium chloride / toluene; ethyl acetate / 2 h / -35 - -25 °C
1.2: 3 h / 10 - 20 °C
2.1: sodium tetrahydroborate; ethanol / 4 h / 10 °C
3.1: triethylamine / dichloromethane / 16 h / 20 °C
4.1: tris-(dibenzylideneacetone)dipalladium(0); 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene; caesium carbonate / 1,4-dioxane / 16 h / 100 °C / Inert atmosphere
5.1: potassium acetate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / 1,4-dioxane / 15 h / 100 °C / Inert atmosphere
6.1: sodium acetate; potassium phosphate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / acetonitrile / 1 h / 100 °C / Sealed tube
View Scheme
Multi-step reaction with 6 steps
1.1: isopropylmagnesium chloride / toluene; ethyl acetate / 2 h / -35 - -25 °C
1.2: 3 h / 10 - 20 °C
2.1: sodium tetrahydroborate; ethanol / 4 h / 10 °C
3.1: pyridine / dichloromethane / 5 h / 0 - 20 °C
4.1: tris-(dibenzylideneacetone)dipalladium(0); 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene; caesium carbonate / 1,4-dioxane / 16 h / 100 °C / Inert atmosphere
5.1: potassium acetate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / 1,4-dioxane / 15 h / 100 °C / Inert atmosphere
6.1: sodium acetate; potassium phosphate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / acetonitrile / 1 h / 100 °C / Sealed tube
View Scheme
1,3-dibromo-2-iodo-5-fluorobenzene
62720-29-0

1,3-dibromo-2-iodo-5-fluorobenzene

(S)-2-(3-(5-(5-(2-ethyl-4-(oxetan-3-yl)piperazin-1-yl)pyridin-2-ylamino)-1-methyl-6-oxo-1,6-dihydropyridin-3-yl)-5-fluoro-2-(hydroxymethyl)phenyl)-3,4,6,7,8,9-hexahydropyrazino[1,2-a]indol-1(2H)-one
1433989-23-1

(S)-2-(3-(5-(5-(2-ethyl-4-(oxetan-3-yl)piperazin-1-yl)pyridin-2-ylamino)-1-methyl-6-oxo-1,6-dihydropyridin-3-yl)-5-fluoro-2-(hydroxymethyl)phenyl)-3,4,6,7,8,9-hexahydropyrazino[1,2-a]indol-1(2H)-one

Conditions
ConditionsYield
Multi-step reaction with 7 steps
1.1: isopropylmagnesium chloride / toluene; ethyl acetate / 2 h / -35 - -25 °C
1.2: 3 h / 10 - 20 °C
2.1: sodium tetrahydroborate; ethanol / 4 h / 10 °C
3.1: triethylamine / dichloromethane / 16 h / 20 °C
4.1: tris-(dibenzylideneacetone)dipalladium(0); 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene; caesium carbonate / 1,4-dioxane / 16 h / 100 °C / Inert atmosphere
5.1: potassium acetate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / 1,4-dioxane / 15 h / 100 °C / Inert atmosphere
6.1: sodium acetate; potassium phosphate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / acetonitrile / 1 h / 100 °C / Sealed tube
7.1: lithium hydroxide; water / isopropyl alcohol; tetrahydrofuran / 1 h / 30 °C
View Scheme
Multi-step reaction with 7 steps
1.1: isopropylmagnesium chloride / toluene; ethyl acetate / 2 h / -35 - -25 °C
1.2: 3 h / 10 - 20 °C
2.1: sodium tetrahydroborate; ethanol / 4 h / 10 °C
3.1: pyridine / dichloromethane / 5 h / 0 - 20 °C
4.1: tris-(dibenzylideneacetone)dipalladium(0); 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene; caesium carbonate / 1,4-dioxane / 16 h / 100 °C / Inert atmosphere
5.1: potassium acetate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / 1,4-dioxane / 15 h / 100 °C / Inert atmosphere
6.1: sodium acetate; potassium phosphate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / acetonitrile / 1 h / 100 °C / Sealed tube
7.1: lithium hydroxide; water / isopropyl alcohol; tetrahydrofuran / 1 h / 30 °C
View Scheme
1,3-dibromo-2-iodo-5-fluorobenzene
62720-29-0

1,3-dibromo-2-iodo-5-fluorobenzene

(S)-4-fluoro-2-(1-methyl-5-(5-(2-methyl-4-(oxetan-3-yl)piperazin-1-yl)pyridin-2-ylamino)-6-oxo-1,6-dihydropyridin-3-yl)-6-(1-oxo-3,4,6,7,8,9-hexahydropyrazino[1,2-a]indol-2(1H)-yl)benzyl acetate
1433989-75-3

(S)-4-fluoro-2-(1-methyl-5-(5-(2-methyl-4-(oxetan-3-yl)piperazin-1-yl)pyridin-2-ylamino)-6-oxo-1,6-dihydropyridin-3-yl)-6-(1-oxo-3,4,6,7,8,9-hexahydropyrazino[1,2-a]indol-2(1H)-yl)benzyl acetate

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1.1: isopropylmagnesium chloride / toluene; ethyl acetate / 2 h / -35 - -25 °C
1.2: 3 h / 10 - 20 °C
2.1: sodium tetrahydroborate; ethanol / 4 h / 10 °C
3.1: triethylamine / dichloromethane / 16 h / 20 °C
4.1: tris-(dibenzylideneacetone)dipalladium(0); 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene; caesium carbonate / 1,4-dioxane / 16 h / 100 °C / Inert atmosphere
5.1: potassium acetate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / 1,4-dioxane / 15 h / 100 °C / Inert atmosphere
6.1: sodium acetate; potassium phosphate tribasic trihydrate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / acetonitrile / 2 h / 110 °C / Sealed tube; Inert atmosphere
View Scheme
Multi-step reaction with 6 steps
1.1: isopropylmagnesium chloride / toluene; ethyl acetate / 2 h / -35 - -25 °C
1.2: 3 h / 10 - 20 °C
2.1: sodium tetrahydroborate; ethanol / 4 h / 10 °C
3.1: pyridine / dichloromethane / 5 h / 0 - 20 °C
4.1: tris-(dibenzylideneacetone)dipalladium(0); 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene; caesium carbonate / 1,4-dioxane / 16 h / 100 °C / Inert atmosphere
5.1: potassium acetate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / 1,4-dioxane / 15 h / 100 °C / Inert atmosphere
6.1: sodium acetate; potassium phosphate tribasic trihydrate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / acetonitrile / 2 h / 110 °C / Sealed tube; Inert atmosphere
View Scheme
1,3-dibromo-2-iodo-5-fluorobenzene
62720-29-0

1,3-dibromo-2-iodo-5-fluorobenzene

(S)-2-(5-fluoro-2-(hydroxymethyl)-3-(1-methyl-5-(5-(2-methyl-4-(oxetan-3-yl)piperazin-1-yl)pyridin-2-ylamino)-6-oxo-1,6-dihydropyridin-3-yl)phenyl)-3,4,6,7,8,9-hexahydropyrazino[1,2-a]indol-1(2H)-one
1433989-25-3

(S)-2-(5-fluoro-2-(hydroxymethyl)-3-(1-methyl-5-(5-(2-methyl-4-(oxetan-3-yl)piperazin-1-yl)pyridin-2-ylamino)-6-oxo-1,6-dihydropyridin-3-yl)phenyl)-3,4,6,7,8,9-hexahydropyrazino[1,2-a]indol-1(2H)-one

Conditions
ConditionsYield
Multi-step reaction with 7 steps
1.1: isopropylmagnesium chloride / toluene; ethyl acetate / 2 h / -35 - -25 °C
1.2: 3 h / 10 - 20 °C
2.1: sodium tetrahydroborate; ethanol / 4 h / 10 °C
3.1: triethylamine / dichloromethane / 16 h / 20 °C
4.1: tris-(dibenzylideneacetone)dipalladium(0); 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene; caesium carbonate / 1,4-dioxane / 16 h / 100 °C / Inert atmosphere
5.1: potassium acetate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / 1,4-dioxane / 15 h / 100 °C / Inert atmosphere
6.1: sodium acetate; potassium phosphate tribasic trihydrate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / acetonitrile / 2 h / 110 °C / Sealed tube; Inert atmosphere
7.1: lithium hydroxide; water / isopropyl alcohol; tetrahydrofuran / 0.5 h
View Scheme
Multi-step reaction with 7 steps
1.1: isopropylmagnesium chloride / toluene; ethyl acetate / 2 h / -35 - -25 °C
1.2: 3 h / 10 - 20 °C
2.1: sodium tetrahydroborate; ethanol / 4 h / 10 °C
3.1: pyridine / dichloromethane / 5 h / 0 - 20 °C
4.1: tris-(dibenzylideneacetone)dipalladium(0); 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene; caesium carbonate / 1,4-dioxane / 16 h / 100 °C / Inert atmosphere
5.1: potassium acetate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / 1,4-dioxane / 15 h / 100 °C / Inert atmosphere
6.1: sodium acetate; potassium phosphate tribasic trihydrate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / acetonitrile / 2 h / 110 °C / Sealed tube; Inert atmosphere
7.1: lithium hydroxide; water / isopropyl alcohol; tetrahydrofuran / 0.5 h
View Scheme
1,3-dibromo-2-iodo-5-fluorobenzene
62720-29-0

1,3-dibromo-2-iodo-5-fluorobenzene

(R)-2-(5-(5-(3,4-Dimethylpiperazin-1-yl)pyridin-2-ylamino)-1-methyl-6-oxo-1,6-dihydropyridin-3-yl)-4-fluoro-6-(1-oxo-3,4,6,7,8,9-hexahydropyrazino[1,2-a]indol-2(1H)-yl)benzyl acetate
1433989-85-5

(R)-2-(5-(5-(3,4-Dimethylpiperazin-1-yl)pyridin-2-ylamino)-1-methyl-6-oxo-1,6-dihydropyridin-3-yl)-4-fluoro-6-(1-oxo-3,4,6,7,8,9-hexahydropyrazino[1,2-a]indol-2(1H)-yl)benzyl acetate

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1.1: isopropylmagnesium chloride / toluene; ethyl acetate / 2 h / -35 - -25 °C
1.2: 3 h / 10 - 20 °C
2.1: sodium tetrahydroborate; ethanol / 4 h / 10 °C
3.1: triethylamine / dichloromethane / 16 h / 20 °C
4.1: tris-(dibenzylideneacetone)dipalladium(0); 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene; caesium carbonate / 1,4-dioxane / 16 h / 100 °C / Inert atmosphere
5.1: potassium acetate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / 1,4-dioxane / 15 h / 100 °C / Inert atmosphere
6.1: sodium acetate; potassium phosphate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / 1,4-dioxane / 2 h / 110 °C
View Scheme
Multi-step reaction with 6 steps
1.1: isopropylmagnesium chloride / toluene; ethyl acetate / 2 h / -35 - -25 °C
1.2: 3 h / 10 - 20 °C
2.1: sodium tetrahydroborate; ethanol / 4 h / 10 °C
3.1: pyridine / dichloromethane / 5 h / 0 - 20 °C
4.1: tris-(dibenzylideneacetone)dipalladium(0); 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene; caesium carbonate / 1,4-dioxane / 16 h / 100 °C / Inert atmosphere
5.1: potassium acetate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / 1,4-dioxane / 15 h / 100 °C / Inert atmosphere
6.1: sodium acetate; potassium phosphate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / 1,4-dioxane / 2 h / 110 °C
View Scheme
1,3-dibromo-2-iodo-5-fluorobenzene
62720-29-0

1,3-dibromo-2-iodo-5-fluorobenzene

(R)-2-(5-((5-(2,4-dimethylpiperazin-1-yl)pyridin-2-yl)amino)-1-methyl-6-oxo-1,6-dihydropyridin-3-yl)-4-fluoro-6-(1-oxo-3,4,6,7,8,9-hexahydropyrazino[1,2-a]indol-2(1H)-yl)benzyl acetate
1433989-93-5

(R)-2-(5-((5-(2,4-dimethylpiperazin-1-yl)pyridin-2-yl)amino)-1-methyl-6-oxo-1,6-dihydropyridin-3-yl)-4-fluoro-6-(1-oxo-3,4,6,7,8,9-hexahydropyrazino[1,2-a]indol-2(1H)-yl)benzyl acetate

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1.1: isopropylmagnesium chloride / toluene; ethyl acetate / 2 h / -35 - -25 °C
1.2: 3 h / 10 - 20 °C
2.1: sodium tetrahydroborate; ethanol / 4 h / 10 °C
3.1: triethylamine / dichloromethane / 16 h / 20 °C
4.1: tris-(dibenzylideneacetone)dipalladium(0); 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene; caesium carbonate / 1,4-dioxane / 16 h / 100 °C / Inert atmosphere
5.1: potassium acetate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / 1,4-dioxane / 15 h / 100 °C / Inert atmosphere
6.1: sodium carbonate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / N,N-dimethyl-formamide / 2 h / 100 °C
View Scheme
Multi-step reaction with 6 steps
1.1: isopropylmagnesium chloride / toluene; ethyl acetate / 2 h / -35 - -25 °C
1.2: 3 h / 10 - 20 °C
2.1: sodium tetrahydroborate; ethanol / 4 h / 10 °C
3.1: pyridine / dichloromethane / 5 h / 0 - 20 °C
4.1: tris-(dibenzylideneacetone)dipalladium(0); 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene; caesium carbonate / 1,4-dioxane / 16 h / 100 °C / Inert atmosphere
5.1: potassium acetate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / 1,4-dioxane / 15 h / 100 °C / Inert atmosphere
6.1: sodium carbonate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / N,N-dimethyl-formamide / 2 h / 100 °C
View Scheme
1,3-dibromo-2-iodo-5-fluorobenzene
62720-29-0

1,3-dibromo-2-iodo-5-fluorobenzene

4-fluoro-2-(5-(5-(3-(fluoromethyl)-4-methylpiperazin-1-yl)pyridin-2-ylamino)-1-methyl-6-oxo-1,6-dihydropyridin-3-yl)-6-(1-oxo-3,4,6,7,8,9-hexa-hydropyrazino[1,2-a]indol-2(1H)-yl)benzyl acetate
1346676-93-4

4-fluoro-2-(5-(5-(3-(fluoromethyl)-4-methylpiperazin-1-yl)pyridin-2-ylamino)-1-methyl-6-oxo-1,6-dihydropyridin-3-yl)-6-(1-oxo-3,4,6,7,8,9-hexa-hydropyrazino[1,2-a]indol-2(1H)-yl)benzyl acetate

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1.1: isopropylmagnesium chloride / toluene; ethyl acetate / 2 h / -35 - -25 °C
1.2: 3 h / 10 - 20 °C
2.1: sodium tetrahydroborate; ethanol / 4 h / 10 °C
3.1: triethylamine / dichloromethane / 16 h / 20 °C
4.1: tris-(dibenzylideneacetone)dipalladium(0); 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene; caesium carbonate / 1,4-dioxane / 16 h / 100 °C / Inert atmosphere
5.1: potassium acetate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / 1,4-dioxane / 15 h / 100 °C / Inert atmosphere
6.1: sodium acetate; potassium phosphate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / acetonitrile; water / 3 h / 110 °C
View Scheme
Multi-step reaction with 6 steps
1.1: isopropylmagnesium chloride / toluene; ethyl acetate / 2 h / -35 - -25 °C
1.2: 3 h / 10 - 20 °C
2.1: sodium tetrahydroborate; ethanol / 4 h / 10 °C
3.1: pyridine / dichloromethane / 5 h / 0 - 20 °C
4.1: tris-(dibenzylideneacetone)dipalladium(0); 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene; caesium carbonate / 1,4-dioxane / 16 h / 100 °C / Inert atmosphere
5.1: potassium acetate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / 1,4-dioxane / 15 h / 100 °C / Inert atmosphere
6.1: sodium acetate; potassium phosphate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / acetonitrile; water / 3 h / 110 °C
View Scheme
1,3-dibromo-2-iodo-5-fluorobenzene
62720-29-0

1,3-dibromo-2-iodo-5-fluorobenzene

2-(5-fluoro-3-(5-(5-(3-(fluoromethyl)-4-methylpiperazin-1-yl)pyridin-2-ylamino)-1-methyl-6-oxo-1,6-dihydropyridin-3-yl)-2-(hydroxymethyl)phenyl)-3,4,6,7,8,9-hexahydropyrazino[1,2-a]indol-1(2H)-one
1346671-86-0

2-(5-fluoro-3-(5-(5-(3-(fluoromethyl)-4-methylpiperazin-1-yl)pyridin-2-ylamino)-1-methyl-6-oxo-1,6-dihydropyridin-3-yl)-2-(hydroxymethyl)phenyl)-3,4,6,7,8,9-hexahydropyrazino[1,2-a]indol-1(2H)-one

Conditions
ConditionsYield
Multi-step reaction with 7 steps
1.1: isopropylmagnesium chloride / toluene; ethyl acetate / 2 h / -35 - -25 °C
1.2: 3 h / 10 - 20 °C
2.1: sodium tetrahydroborate; ethanol / 4 h / 10 °C
3.1: triethylamine / dichloromethane / 16 h / 20 °C
4.1: tris-(dibenzylideneacetone)dipalladium(0); 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene; caesium carbonate / 1,4-dioxane / 16 h / 100 °C / Inert atmosphere
5.1: potassium acetate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / 1,4-dioxane / 15 h / 100 °C / Inert atmosphere
6.1: sodium acetate; potassium phosphate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / acetonitrile; water / 3 h / 110 °C
7.1: lithium hydroxide monohydrate / water; isopropyl alcohol; tetrahydrofuran / 1 h / 30 °C
View Scheme
Multi-step reaction with 7 steps
1.1: isopropylmagnesium chloride / toluene; ethyl acetate / 2 h / -35 - -25 °C
1.2: 3 h / 10 - 20 °C
2.1: sodium tetrahydroborate; ethanol / 4 h / 10 °C
3.1: pyridine / dichloromethane / 5 h / 0 - 20 °C
4.1: tris-(dibenzylideneacetone)dipalladium(0); 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene; caesium carbonate / 1,4-dioxane / 16 h / 100 °C / Inert atmosphere
5.1: potassium acetate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / 1,4-dioxane / 15 h / 100 °C / Inert atmosphere
6.1: sodium acetate; potassium phosphate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / acetonitrile; water / 3 h / 110 °C
7.1: lithium hydroxide monohydrate / water; isopropyl alcohol; tetrahydrofuran / 1 h / 30 °C
View Scheme
1,3-dibromo-2-iodo-5-fluorobenzene
62720-29-0

1,3-dibromo-2-iodo-5-fluorobenzene

4-fluoro-2-(1-methyl-5-(5-(9-methyl-7-oxa-3,9-diaza-bicyclo-[3.3.1]nonan-3-yl)pyridin-2-ylamino)-6-oxo-1,6-dihydropyridin-3-yl)-6-(1-oxo-3,4,6,7,8,9-hexahydropyrazino[1,2-a]indol-2(1H)-yl)benzyl acetate
1433990-08-9

4-fluoro-2-(1-methyl-5-(5-(9-methyl-7-oxa-3,9-diaza-bicyclo-[3.3.1]nonan-3-yl)pyridin-2-ylamino)-6-oxo-1,6-dihydropyridin-3-yl)-6-(1-oxo-3,4,6,7,8,9-hexahydropyrazino[1,2-a]indol-2(1H)-yl)benzyl acetate

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1.1: isopropylmagnesium chloride / toluene; ethyl acetate / 2 h / -35 - -25 °C
1.2: 3 h / 10 - 20 °C
2.1: sodium tetrahydroborate; ethanol / 4 h / 10 °C
3.1: triethylamine / dichloromethane / 16 h / 20 °C
4.1: tris-(dibenzylideneacetone)dipalladium(0); 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene; caesium carbonate / 1,4-dioxane / 16 h / 100 °C / Inert atmosphere
5.1: potassium acetate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / 1,4-dioxane / 15 h / 100 °C / Inert atmosphere
6.1: sodium acetate; potassium phosphate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / acetonitrile; water / 3 h / 110 °C
View Scheme
Multi-step reaction with 6 steps
1.1: isopropylmagnesium chloride / toluene; ethyl acetate / 2 h / -35 - -25 °C
1.2: 3 h / 10 - 20 °C
2.1: sodium tetrahydroborate; ethanol / 4 h / 10 °C
3.1: pyridine / dichloromethane / 5 h / 0 - 20 °C
4.1: tris-(dibenzylideneacetone)dipalladium(0); 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene; caesium carbonate / 1,4-dioxane / 16 h / 100 °C / Inert atmosphere
5.1: potassium acetate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / 1,4-dioxane / 15 h / 100 °C / Inert atmosphere
6.1: sodium acetate; potassium phosphate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / acetonitrile; water / 3 h / 110 °C
View Scheme
1,3-dibromo-2-iodo-5-fluorobenzene
62720-29-0

1,3-dibromo-2-iodo-5-fluorobenzene

2-bromo-6-(7,7-difluoro-1-oxo-3,4,6,7,8,9-hexahydropyrazino[1,2-a]indol-2(1H)-yl)-4-fluorobenzyl Acetate
1433990-15-8

2-bromo-6-(7,7-difluoro-1-oxo-3,4,6,7,8,9-hexahydropyrazino[1,2-a]indol-2(1H)-yl)-4-fluorobenzyl Acetate

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1.1: isopropylmagnesium chloride / toluene; ethyl acetate / 2 h / -35 - -25 °C
1.2: 3 h / 10 - 20 °C
2.1: sodium tetrahydroborate; ethanol / 4 h / 10 °C
3.1: triethylamine / dichloromethane / 16 h / 20 °C
4.1: tris-(dibenzylideneacetone)dipalladium(0); 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene; caesium carbonate / 1,4-dioxane / 16 h / 100 °C / Inert atmosphere
View Scheme
Multi-step reaction with 4 steps
1.1: isopropylmagnesium chloride / toluene; ethyl acetate / 2 h / -35 - -25 °C
1.2: 3 h / 10 - 20 °C
2.1: sodium tetrahydroborate; ethanol / 4 h / 10 °C
3.1: pyridine / dichloromethane / 5 h / 0 - 20 °C
4.1: tris-(dibenzylideneacetone)dipalladium(0); 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene; caesium carbonate / 1,4-dioxane / 16 h / 100 °C / Inert atmosphere
View Scheme
1,3-dibromo-2-iodo-5-fluorobenzene
62720-29-0

1,3-dibromo-2-iodo-5-fluorobenzene

(S)-2-(7,7-difluoro-1-oxo-3,4,6,7,8,9-hexahydropyrazino[1,2-a]indol-2(1H)-yl)-4-fluoro-6-(1-methyl-5-(5-(2-methyl-4-(oxetan-3-yl)piperazin-1-yl)pyridin-2-ylamino)-6-oxo-1,6-dihydropyridin-3-yl)benzyl Acetate
1433990-16-9

(S)-2-(7,7-difluoro-1-oxo-3,4,6,7,8,9-hexahydropyrazino[1,2-a]indol-2(1H)-yl)-4-fluoro-6-(1-methyl-5-(5-(2-methyl-4-(oxetan-3-yl)piperazin-1-yl)pyridin-2-ylamino)-6-oxo-1,6-dihydropyridin-3-yl)benzyl Acetate

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1.1: isopropylmagnesium chloride / toluene; ethyl acetate / 2 h / -35 - -25 °C
1.2: 3 h / 10 - 20 °C
2.1: sodium tetrahydroborate; ethanol / 4 h / 10 °C
3.1: triethylamine / dichloromethane / 16 h / 20 °C
4.1: tris-(dibenzylideneacetone)dipalladium(0); 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene; caesium carbonate / 1,4-dioxane / 16 h / 100 °C / Inert atmosphere
5.1: sodium acetate; potassium phosphate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / acetonitrile; water / 1 h / 100 °C
View Scheme
Multi-step reaction with 5 steps
1.1: isopropylmagnesium chloride / toluene; ethyl acetate / 2 h / -35 - -25 °C
1.2: 3 h / 10 - 20 °C
2.1: sodium tetrahydroborate; ethanol / 4 h / 10 °C
3.1: pyridine / dichloromethane / 5 h / 0 - 20 °C
4.1: tris-(dibenzylideneacetone)dipalladium(0); 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene; caesium carbonate / 1,4-dioxane / 16 h / 100 °C / Inert atmosphere
5.1: sodium acetate; potassium phosphate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / acetonitrile; water / 1 h / 100 °C
View Scheme
1,3-dibromo-2-iodo-5-fluorobenzene
62720-29-0

1,3-dibromo-2-iodo-5-fluorobenzene

(S)-7,7-difluoro-2-(5-fluoro-2-(hydroxymethyl)-3-(1-methyl-5-(5-(2-methyl-4-(oxetan-3-yl)piperazin-1-yl)pyridin-2-ylamino)-6-oxo-1,6-dihydropyridin-3-yl)phenyl)-3,4,6,7,8,9-hexahydropyrazino[1,2-a]indol-1(2H)-one
1433989-42-4

(S)-7,7-difluoro-2-(5-fluoro-2-(hydroxymethyl)-3-(1-methyl-5-(5-(2-methyl-4-(oxetan-3-yl)piperazin-1-yl)pyridin-2-ylamino)-6-oxo-1,6-dihydropyridin-3-yl)phenyl)-3,4,6,7,8,9-hexahydropyrazino[1,2-a]indol-1(2H)-one

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1.1: isopropylmagnesium chloride / toluene; ethyl acetate / 2 h / -35 - -25 °C
1.2: 3 h / 10 - 20 °C
2.1: sodium tetrahydroborate; ethanol / 4 h / 10 °C
3.1: triethylamine / dichloromethane / 16 h / 20 °C
4.1: tris-(dibenzylideneacetone)dipalladium(0); 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene; caesium carbonate / 1,4-dioxane / 16 h / 100 °C / Inert atmosphere
5.1: sodium acetate; potassium phosphate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / acetonitrile; water / 1 h / 100 °C
6.1: lithium hydroxide / water; isopropyl alcohol; tetrahydrofuran / 1 h / 30 °C
View Scheme
Multi-step reaction with 6 steps
1.1: isopropylmagnesium chloride / toluene; ethyl acetate / 2 h / -35 - -25 °C
1.2: 3 h / 10 - 20 °C
2.1: sodium tetrahydroborate; ethanol / 4 h / 10 °C
3.1: pyridine / dichloromethane / 5 h / 0 - 20 °C
4.1: tris-(dibenzylideneacetone)dipalladium(0); 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene; caesium carbonate / 1,4-dioxane / 16 h / 100 °C / Inert atmosphere
5.1: sodium acetate; potassium phosphate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / acetonitrile; water / 1 h / 100 °C
6.1: lithium hydroxide / water; isopropyl alcohol; tetrahydrofuran / 1 h / 30 °C
View Scheme
1,3-dibromo-2-iodo-5-fluorobenzene
62720-29-0

1,3-dibromo-2-iodo-5-fluorobenzene

2,6-dibromo-4-fluorobenzyl acetate
1346674-62-1

2,6-dibromo-4-fluorobenzyl acetate

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: isopropylmagnesium chloride / toluene; ethyl acetate / 2 h / -35 - -25 °C
1.2: 3 h / 10 - 20 °C
2.1: sodium tetrahydroborate; ethanol / 4 h / 10 °C
3.1: triethylamine / dichloromethane / 16 h / 20 °C
View Scheme
Multi-step reaction with 3 steps
1.1: isopropylmagnesium chloride / toluene; ethyl acetate / 2 h / -35 - -25 °C
1.2: 3 h / 10 - 20 °C
2.1: sodium tetrahydroborate; ethanol / 4 h / 10 °C
3.1: pyridine / dichloromethane / 5 h / 0 - 20 °C
View Scheme
Multi-step reaction with 4 steps
1: hydrogenchloride / toluene; diethyl ether / 2 h / -35 - -25 °C
2: toluene; diethyl ether / 3 h / -25 - 10 °C
3: sodium tetrahydroborate / ethanol / 4 h / 10 °C
4: pyridine / dichloromethane / 5 h / 0 - 20 °C
View Scheme
Multi-step reaction with 3 steps
1.1: diethyl ether; toluene / 2 h / -35 - -25 °C
1.2: 3 h / -19 - 10 °C
2.1: sodium tetrahydroborate / ethanol / 4 h / 10 °C
3.1: triethylamine / dichloromethane / 16 h / 10 °C / Inert atmosphere
View Scheme
1,3-dibromo-2-iodo-5-fluorobenzene
62720-29-0

1,3-dibromo-2-iodo-5-fluorobenzene

(S)-2-(6-tert-butyl-8-fluoro-1-oxophthalazin-2(1H)-yl)-4-fluoro-6-(1-methyl-5-(5-(2-methyl-4-(oxetan-3-yl)piperazin-1-yl)pyridin-2-ylamino)-6-oxo-1,6-dihydropyridin-3-yl)benzaldehyde
1433849-48-9

(S)-2-(6-tert-butyl-8-fluoro-1-oxophthalazin-2(1H)-yl)-4-fluoro-6-(1-methyl-5-(5-(2-methyl-4-(oxetan-3-yl)piperazin-1-yl)pyridin-2-ylamino)-6-oxo-1,6-dihydropyridin-3-yl)benzaldehyde

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: isopropylmagnesium chloride / toluene; diethyl ether / 1.5 h / -35 - -25 °C
1.2: 1.5 h / -19 - 10 °C
2.1: potassium acetate; 4,7-dimethoxy-1,10-phenanthroline; copper(l) iodide / 1,4-dioxane / 10 h / 90 °C / Inert atmosphere
3.1: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; sodium acetate; potassium phosphate / tetrahydrofuran; water / 2 h / 100 °C / Inert atmosphere
View Scheme
1,3-dibromo-2-iodo-5-fluorobenzene
62720-29-0

1,3-dibromo-2-iodo-5-fluorobenzene

(2-{4,4-dimethyl-9-oxo-1,10-diazatricyclo[6.4.0.02,6]dodeca-2(6),7-dien-10-yl}-6-[5-({5-[(2S)-2-ethyl-4-(oxetan-3-yl)piperazin-1-yl]pyridin-2-yl}amino)-1-methyl-6-oxo-1,6-dihydropyridin-3-yl]-4-fluorophenyl)methyl Acetate
1433990-17-0

(2-{4,4-dimethyl-9-oxo-1,10-diazatricyclo[6.4.0.02,6]dodeca-2(6),7-dien-10-yl}-6-[5-({5-[(2S)-2-ethyl-4-(oxetan-3-yl)piperazin-1-yl]pyridin-2-yl}amino)-1-methyl-6-oxo-1,6-dihydropyridin-3-yl]-4-fluorophenyl)methyl Acetate

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1.1: isopropylmagnesium chloride / toluene; ethyl acetate / 2 h / -35 - -25 °C
1.2: 3 h / 10 - 20 °C
2.1: sodium tetrahydroborate; ethanol / 4 h / 10 °C
3.1: triethylamine / dichloromethane / 16 h / 20 °C
4.1: caesium carbonate / 1,4-dioxane / 0.5 h / Sealed tube
4.2: 16 h / 100 °C
5.1: potassium acetate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 / dichloromethane; 1,4-dioxane / 5 h / 100 °C
6.1: sodium acetate; potassium phosphate / acetonitrile; water / 2 h / Reflux
View Scheme
Multi-step reaction with 6 steps
1.1: isopropylmagnesium chloride / toluene; ethyl acetate / 2 h / -35 - -25 °C
1.2: 3 h / 10 - 20 °C
2.1: sodium tetrahydroborate; ethanol / 4 h / 10 °C
3.1: pyridine / dichloromethane / 5 h / 0 - 20 °C
4.1: caesium carbonate / 1,4-dioxane / 0.5 h / Sealed tube
4.2: 16 h / 100 °C
5.1: potassium acetate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 / dichloromethane; 1,4-dioxane / 5 h / 100 °C
6.1: sodium acetate; potassium phosphate / acetonitrile; water / 2 h / Reflux
View Scheme

1,3-Dibromo-5-fluoro-2-iodobenzene Specification

The Benzene,1,3-dibromo-5-fluoro-2-iodo-, with CAS registry number 62720-29-0, belongs to the following product categories: (1)Bromine Compounds; (2)Fluorine Compounds; (3)Iodine Compounds. It has the systematic name of 1,3-dibromo-5-fluoro-2-iodobenzene. This chemical is a kind of beige to pinkish or pale brown.

Physical properties of Benzene,1,3-dibromo-5-fluoro-2-iodo-: (1)ACD/LogP: 4.53; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 4.53; (4)ACD/LogD (pH 7.4): 4.53; (5)ACD/BCF (pH 5.5): 1643.07; (6)ACD/BCF (pH 7.4): 1643.07; (7)ACD/KOC (pH 5.5): 6972.13; (8)ACD/KOC (pH 7.4): 6972.13; (9)#H bond acceptors: 0; (10)#H bond donors: 0; (11)#Freely Rotating Bonds: 0; (12)Polar Surface Area: 0 Å2; (13)Index of Refraction: 1.657; (14)Molar Refractivity: 54.53 cm3; (15)Molar Volume: 148 cm3; (16)Polarizability: 21.61×10-24cm3; (17)Surface Tension: 48.6 dyne/cm; (18)Enthalpy of Vaporization: 51.1 kJ/mol; (19)Vapour Pressure: 0.00313 mmHg at 25°C.

Preparation: this chemical can be prepared by C10H12Br2FN3. This reaction will need reagent aq. HI and solvent acetonitrile.  The reaction time is 90 min with reaction temperature of 60 ℃. The yield is about 71%.

When you are using this chemical, please be cautious about it as the following:
The Benzene,1,3-dibromo-5-fluoro-2-iodo- irritates to eyes, respiratory system and skin. When use this chemical, avoid contact with skin and eyes.

You can still convert the following datas into molecular structure:
(1)SMILES: Brc1cc(F)cc(Br)c1I
(2)InChI: InChI=1/C6H2Br2FI/c7-4-1-3(9)2-5(8)6(4)10/h1-2H
(3)InChIKey: LIWKANDEJFABTQ-UHFFFAOYAW
(4)Std. InChI: InChI=1S/C6H2Br2FI/c7-4-1-3(9)2-5(8)6(4)10/h1-2H
(5)Std. InChIKey: LIWKANDEJFABTQ-UHFFFAOYSA-N

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