5-Bromo-7-azaindole supplier | CasNO.183208-35-7

Name
5-Bromo-7-azaindole
EINECS 629-247-8
CAS No. 183208-35-7
Article Data42
CAS DataBase
Density 1.77 g/cm³
Solubility
Melting Point 178.0-178.8 °C
Formula C₇H₅BrN₂
Boiling Point 357.4±42.0 °C(Predicted)
Molecular Weight 197.034
Flash Point
Transport Information
Appearance
Safety 26-39
Risk Codes 22-41
Molecular Structure
Hazard Symbols Xi,Xn
Synonyms 5-Bromo-7-azaindole;7-aza-5-bromoindole;5-Bromo-1H-pyrrolo[2,3-b]pyridine;5-BROMO AZAINDOLE;RW2897;
PSA 28.68000
LogP 2.32540

Synthetic route

: 115170-40-6
7-aza-5-bromoindoline

: 183208-35-7
5-bromo-1H-pyrrolo[2,3-b]pyridine

Conditions

Conditions	Yield
With manganese(IV) oxide In dichloromethane for 72h;	100%
With manganese(IV) oxide In toluene for 4h; Reflux;	90%
With activated carbon fiber catalyst In 5,5-dimethyl-1,3-cyclohexadiene at 100℃; for 8h; Solvent;	85.43%

: 754214-54-5
5-bromo-1-(tert-butyl-dimethyl-silanyl)-1H-pyrrolo[2,3-b]pyridine

: 183208-35-7
5-bromo-1H-pyrrolo[2,3-b]pyridine

Conditions

Conditions	Yield
With hydrogenchloride In methanol for 0.133333h;	94%
With tetrabutyl ammonium fluoride In tetrahydrofuran at 25℃; for 0.5h;

2-nitro-3-dimethylaminovinyl-5-bromopyridine: 2-nitro-3-dimethylaminovinyl-5-bromopyridine

: 183208-35-7
5-bromo-1H-pyrrolo[2,3-b]pyridine

Conditions

Conditions	Yield
With sodium at 20 - 60℃; for 1.5h; Temperature; Inert atmosphere;	92.9%

Conditions

Conditions	Yield
With potassium hydroxide In 1,2-dimethoxyethane at 140℃; for 16h; Industrial scale;	91.5%

5-bromo-3-ethynyl-pyridin-2-ylamine: 5-bromo-3-ethynyl-pyridin-2-ylamine

: 183208-35-7
5-bromo-1H-pyrrolo[2,3-b]pyridine

Conditions

Conditions	Yield
With potassium tert-butylate In N,N-dimethyl-formamide at 60 - 85℃; Large scale;	90%
Stage #1: 5-bromo-3-ethynyl-pyridin-2-ylamine With potassium tert-butylate In 1-methyl-pyrrolidin-2-one at 60℃; for 3h; Stage #2: With water In 1-methyl-pyrrolidin-2-one; toluene

: (E)-N'-(5-bromo-3-methylpyridin-2-yl)-N-methyl-N-phenylmethanimidamide

: 183208-35-7
5-bromo-1H-pyrrolo[2,3-b]pyridine

Conditions

Conditions	Yield
With sodium amide In diethylene glycol dimethyl ether at 10 - 15℃; for 16h; Industrial scale;	87.6%

: C9H13Br2NO3

: 183208-35-7
5-bromo-1H-pyrrolo[2,3-b]pyridine

Conditions

Conditions	Yield
With ammonium hydroxide; potassium carbonate; ammonium chloride In tetrahydrofuran at 25 - 60℃; for 4h;	86.8%

: 1262985-25-0
4-(2-amino-5-bromopyridin-3-yl)-2-methylbut-3-yn-2-ol

: 183208-35-7
5-bromo-1H-pyrrolo[2,3-b]pyridine

Conditions

Conditions	Yield
With sodium hydroxide In water; glycerol at 80℃; for 15h; Solvent;	86.6%
With sodium hydroxide In 1-methyl-pyrrolidin-2-one; water at 75 - 81℃; under 262.526 Torr; Inert atmosphere;	75%

: 4458-15-5
2-aminopyrrole

: bromomalonaldehyde; sodium enolate

: 183208-35-7
5-bromo-1H-pyrrolo[2,3-b]pyridine

Conditions

Conditions	Yield
With hydrogen bromide In ethanol Reflux;	85.5%

: 905966-34-9
5-bromo-3-(2-(trimethylsilyl)ethynyl)pyridine-2-amine

: 183208-35-7
5-bromo-1H-pyrrolo[2,3-b]pyridine

Conditions

Conditions	Yield
With sodium hydride In 1-methyl-pyrrolidin-2-one at 80℃; for 1h; Inert atmosphere;	80%
With potassium tert-butylate In 1-methyl-pyrrolidin-2-one at 80℃; for 1h;	70%
Stage #1: 5-bromo-3-(2-(trimethylsilyl)ethynyl)pyridine-2-amine With potassium tert-butylate In tert-butyl alcohol for 12h; Heating / reflux; Stage #2: With hydrogenchloride In water; tert-butyl alcohol at 20℃; for 12h; Heating / reflux; Stage #3: With sodium hydroxide In water; tert-butyl alcohol	60%
Stage #1: 5-bromo-3-(2-(trimethylsilyl)ethynyl)pyridine-2-amine With potassium tert-butylate In tert-butyl alcohol Stage #2: With hydrogenchloride In water; tert-butyl alcohol	56%
With potassium tert-butylate In 1-methyl-pyrrolidin-2-one at 20 - 80℃; for 1h; Product distribution / selectivity;	53%

: 183208-34-6
5-bromo-1,3-dihydro-2H-pyrrolo[2,3-b]pyridin-2-one

: 183208-35-7
5-bromo-1H-pyrrolo[2,3-b]pyridine

Conditions

Conditions	Yield
Stage #1: 5-bromo-1,3-dihydro-2H-pyrrolo[2,3-b]pyridin-2-one With hydrogenchloride; tin In ethanol; water at 40℃; for 2h; Stage #2: With copper(ll) bromide In chloroform at 60℃; for 2h; Solvent; Temperature; Reagent/catalyst;	77.6%
Stage #1: 5-bromo-1,3-dihydro-2H-pyrrolo[2,3-b]pyridin-2-one With borane-THF In tetrahydrofuran at 0 - 20℃; for 0.583333h; Stage #2: With manganese triacetate In acetic acid at 75℃; for 0.75h;	50%
Stage #1: 5-bromo-1,3-dihydro-2H-pyrrolo[2,3-b]pyridin-2-one With borane-THF In tetrahydrofuran at 20℃; for 0.833333h; Stage #2: With manganese triacetate; acetic acid at 75℃; for 0.833333h; Further stages.;	50%
Stage #1: 5-bromo-1,3-dihydro-2H-pyrrolo[2,3-b]pyridin-2-one With borane-THF In tetrahydrofuran at 0 - 20℃; Stage #2: With manganese(III) triacetate dihydrate; acetic acid In tetrahydrofuran at 75℃;	50%
With hydrogenchloride; borane-THF; manganese triacetate 1.) THF, 0 deg C, 35 min, RT, 2.) H2O, reflux, 3.) acetic acid, 45 min, 75 deg C; Yield given; Multistep reaction;

: 1743-36-8
1-phenylbut-3-yn-1-ol

: 183208-35-7
5-bromo-1H-pyrrolo[2,3-b]pyridine

Conditions

Conditions	Yield
With di-isopropyl azodicarboxylate; diphenyl phosphoryl azide; triphenylphosphine In tetrahydrofuran at 20℃; for 24h;	75%

: 875639-46-6
N-(5-bromo-3-trimethylsilanylethynyl-pyridin-2-yl)-acetamide

: 183208-35-7
5-bromo-1H-pyrrolo[2,3-b]pyridine

Conditions

Conditions	Yield
With tetrabutyl ammonium fluoride In tetrahydrofuran for 15h; Heating / reflux;	67%
With tetrabutyl ammonium fluoride In tetrahydrofuran for 15h; Heating / reflux;	67%

: N'-(5-bromo-3-methylpyridin-2-yl)-N-methyl-N-phenylmethanimidamide

: 183208-35-7
5-bromo-1H-pyrrolo[2,3-b]pyridine

Conditions

Conditions	Yield
With sodium amide; N-methylaniline for 2h; Reagent/catalyst; Temperature; Inert atmosphere; Reflux;	60%

: 883052-76-4
N'-(5-bromo-3-methyl-pyridin-2-yl)-N,N-dimethyl-formamidine

: 183208-35-7
5-bromo-1H-pyrrolo[2,3-b]pyridine

Conditions

Conditions	Yield
Stage #1: N'-(5-bromo-3-methyl-pyridin-2-yl)-N,N-dimethyl-formamidine With lithium diisopropyl amide In tetrahydrofuran at -30℃; Stage #2: With acetic acid In tetrahydrofuran Product distribution / selectivity;	26%
Stage #1: N'-(5-bromo-3-methyl-pyridin-2-yl)-N,N-dimethyl-formamidine With lithium diisopropyl amide In tetrahydrofuran at -30℃; Stage #2: With acetic acid In tetrahydrofuran Product distribution / selectivity;	26%

: (E)-N’-(5-bromo-3-methylpyridin-2-yl)-N,N-dimethylformimidamide

: 183208-35-7
5-bromo-1H-pyrrolo[2,3-b]pyridine

Conditions

Conditions	Yield
Stage #1: (E)-N’-(5-bromo-3-methylpyridin-2-yl)-N,N-dimethylformimidamide With lithium diisopropyl amide In tetrahydrofuran at -30℃; for 5 - 6h; Stage #2: With acetic acid In tetrahydrofuran for 0.166667h; Product distribution / selectivity;	26%

: 5-bromo-1H-pyrrolo[2,3-b]pyridin-2(3H)-one

: 183208-35-7
5-bromo-1H-pyrrolo[2,3-b]pyridine

Conditions

Conditions	Yield
Stage #1: 5-bromo-1H-pyrrolo[2,3-b]pyridin-2(3H)-one With diborane In tetrahydrofuran at 20℃; for 0.833333h; Inert atmosphere; Stage #2: With manganese triacetate In acetic acid at 75℃; for 0.833333h;	6%

: 271-63-6
7-Azaindole

n-pentyl halide: n-pentyl halide

: 183208-35-7
5-bromo-1H-pyrrolo[2,3-b]pyridine

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1.1: 85 percent / bromine / 2-methyl-propan-2-ol; H2O / 24 h / 24.84 °C 2.1: 95 percent / zinc; acetic acid / 5 h / 20 °C 3.1: BH3THF / tetrahydrofuran / 0.83 h / 20 °C 3.2: 50 percent / Mn(OAc)32H2O; acetic acid / 0.83 h / 75 °C View Scheme

: 183208-32-4
3,3,5-Tribromo-1,3-dihydro-2H-pyrrolo[2,3-b]pyridin-2-one

: 183208-35-7
5-bromo-1H-pyrrolo[2,3-b]pyridine

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1.1: 95 percent / zinc; acetic acid / 5 h / 20 °C 2.1: BH3THF / tetrahydrofuran / 0.83 h / 20 °C 2.2: 50 percent / Mn(OAc)32H2O; acetic acid / 0.83 h / 75 °C View Scheme
Multi-step reaction with 2 steps 1.1: 94 percent / zinc; acetic acid / 20 °C 2.1: borane*tetrahydrofurane / tetrahydrofuran / 0.58 h / 0 - 20 °C 2.2: 50 percent / manganese triacetate / acetic acid / 0.75 h / 75 °C View Scheme
Multi-step reaction with 2 steps 1: 94 percent / zinc, acetic acid / 3 h / Ambient temperature 2: 1.) borane-THF complex, 2.) 6N HCl, 3.) manganese(III) acetate / 1.) THF, 0 deg C, 35 min, RT, 2.) H2O, reflux, 3.) acetic acid, 45 min, 75 deg C View Scheme
Multi-step reaction with 2 steps 1.1: zinc; acetic acid / 20 °C 2.1: borane-THF / tetrahydrofuran / 0 - 20 °C 2.2: 75 °C View Scheme

: 271-63-6
7-Azaindole

: 183208-35-7
5-bromo-1H-pyrrolo[2,3-b]pyridine

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1.1: 85 percent / bromine / 2-methyl-propan-2-ol; H2O / 20 °C 2.1: 94 percent / zinc; acetic acid / 20 °C 3.1: borane*tetrahydrofurane / tetrahydrofuran / 0.58 h / 0 - 20 °C 3.2: 50 percent / manganese triacetate / acetic acid / 0.75 h / 75 °C View Scheme
Multi-step reaction with 3 steps 1: 85 percent / bromine / 2-methyl-propan-2-ol; H2O / 19 h / Ambient temperature 2: 94 percent / zinc, acetic acid / 3 h / Ambient temperature 3: 1.) borane-THF complex, 2.) 6N HCl, 3.) manganese(III) acetate / 1.) THF, 0 deg C, 35 min, RT, 2.) H2O, reflux, 3.) acetic acid, 45 min, 75 deg C View Scheme

: 1111638-00-6
C11H15BrN2O

: 183208-35-7
5-bromo-1H-pyrrolo[2,3-b]pyridine

Conditions

Conditions	Yield
Stage #1: C11H15BrN2O With hydrogenchloride In water for 8h; Heating / reflux; Stage #2: With sodium hydroxide; water

: 1-(tert-butyl-dimethyl-silanyl)-2,3-dihydro-1H-pyrrolo[2,3-b]pyridine

: 183208-35-7
5-bromo-1H-pyrrolo[2,3-b]pyridine

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: bromine; pyridine / dichloromethane / 2 h / 0 °C 2: 2,3-dicyano-5,6-dichloro-p-benzoquinone / dichloromethane / 1 h 3: tetrabutyl ammonium fluoride / tetrahydrofuran / 0.5 h / 25 °C View Scheme

: 5-bromo-1-(tert-butyl-dimethyl-silanyl)-2,3-dihydro-1H-pyrrolo[2,3-b]pyridine

: 183208-35-7
5-bromo-1H-pyrrolo[2,3-b]pyridine

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 2,3-dicyano-5,6-dichloro-p-benzoquinone / dichloromethane / 1 h 2: tetrabutyl ammonium fluoride / tetrahydrofuran / 0.5 h / 25 °C View Scheme

: 10592-27-5
7-azaindoline

: 183208-35-7
5-bromo-1H-pyrrolo[2,3-b]pyridine

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.5 h / 0 °C 1.2: 3 h / 0 °C 2.1: bromine; pyridine / dichloromethane / 2 h / 0 °C 3.1: 2,3-dicyano-5,6-dichloro-p-benzoquinone / dichloromethane / 1 h 4.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 0.5 h / 25 °C View Scheme
Multi-step reaction with 2 steps 1: 1,3-dibromo-5,5-dimethylimidazolidine-2,4-dione; toluene-4-sulfonic acid / dichloromethane / 1 h / 20 °C 2: manganese(IV) oxide / toluene / 1 h / 90 °C View Scheme

: 381233-96-1
2-amino-3-iodo-5-bromopyridine

: 183208-35-7
5-bromo-1H-pyrrolo[2,3-b]pyridine

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: lithium hydroxide / dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 / N,N-dimethyl-formamide / 18 h / 70 °C 2: hydrogenchloride / water / 1 h / 50 °C View Scheme
Multi-step reaction with 2 steps 1: copper(l) iodide; bis-triphenylphosphine-palladium(II) chloride; triethylamine / 1 h / 20 °C / Inert atmosphere 2: sodium hydride / 1-methyl-pyrrolidin-2-one / 1 h / 80 °C / Inert atmosphere View Scheme
Multi-step reaction with 2 steps 1: triethylamine; copper(l) iodide; bis-triphenylphosphine-palladium(II) chloride / tetrahydrofuran / 3 h / 20 °C / Inert atmosphere 2: potassium tert-butylate / 1-methyl-pyrrolidin-2-one / 1 h / 80 °C View Scheme

: 1072-97-5
5-bromo-2-pyridylamine

: 183208-35-7
5-bromo-1H-pyrrolo[2,3-b]pyridine

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: trifluoroacetic acid; sodium periodate; iodine / acetonitrile / 80 °C 2: lithium hydroxide / dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 / N,N-dimethyl-formamide / 18 h / 70 °C 3: hydrogenchloride / water / 1 h / 50 °C View Scheme
Multi-step reaction with 3 steps 1: trifluoroacetic acid; sodium periodate; iodine / acetonitrile / 80 °C 2: N,N,N',N'-tetramethylguanidine; copper(l) iodide / bis-triphenylphosphine-palladium(II) chloride / toluene / 1 h / 80 °C / Inert atmosphere 3: potassium tert-butylate / 1-methyl-pyrrolidin-2-one / 1 h / 20 - 80 °C View Scheme
Multi-step reaction with 3 steps 1.1: trifluoroacetic acid; N-iodo-succinimide / N,N-dimethyl-formamide / 3 h / 20 - 50 °C 1.2: pH 7 2.1: lithium hydroxide / dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 / 18 h / 70 °C 3.1: hydrogenchloride / water / 1 h / 50 °C View Scheme
Multi-step reaction with 3 steps 1: periodic acid; iodine / acetonitrile / Inert atmosphere 2: copper(l) iodide; bis-triphenylphosphine-palladium(II) chloride; triethylamine / 1 h / 20 °C / Inert atmosphere 3: sodium hydride / 1-methyl-pyrrolidin-2-one / 1 h / 80 °C / Inert atmosphere View Scheme
Multi-step reaction with 3 steps 1: acetic acid; sodium periodate; iodine / 2 h / 80 °C 2: dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; copper(l) iodide; triethylamine / dichloromethane / 30 h / Inert atmosphere; Reflux 3: sodium hydroxide / water; glycerol / 15 h / 80 °C View Scheme

: 1356397-50-6
C9H11BrN2O

: 183208-35-7
5-bromo-1H-pyrrolo[2,3-b]pyridine

Conditions

Conditions	Yield
With hydrogenchloride In water at 50℃; for 1h; Product distribution / selectivity;
With hydrogenchloride In water at 50℃; for 1h;

: 3430-21-5
5-bromo-3-methyl-pyridin-2-ylamine

: 183208-35-7
5-bromo-1H-pyrrolo[2,3-b]pyridine

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: toluene-4-sulfonic acid / 1 h / 85 °C 2: 2 h / 110 °C 3: N-methylaniline; sodium amide / 2 h / Inert atmosphere; Reflux View Scheme
Multi-step reaction with 3 steps 1: toluene-4-sulfonic acid / dichloromethane / 16 h / Reflux; Industrial scale 2: toluene / 16 h / 60 °C / Industrial scale 3: sodium amide / diethylene glycol dimethyl ether / 16 h / 10 - 15 °C / Industrial scale View Scheme

: 35486-42-1
2-amino-3,5-dibromopyridine

: 183208-35-7
5-bromo-1H-pyrrolo[2,3-b]pyridine

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1.1: toluene-4-sulfonic acid / 5 h / 95 °C / Industrial scale 2.1: sodium hydride / 1,4-dioxane / 2 h / Industrial scale 2.2: 14 h / 80 °C / Industrial scale 3.1: potassium hydroxide / 1,2-dimethoxyethane / 16 h / 140 °C / Industrial scale View Scheme

: 183208-35-7
5-bromo-1H-pyrrolo[2,3-b]pyridine

: 74-88-4
methyl iodide

: 183208-22-2
5-bromo-1-methyl-1H-pyrrolo[2,3-b]pyridine

Conditions

Conditions	Yield
Stage #1: 5-bromo-1H-pyrrolo[2,3-b]pyridine With sodium hydride In N,N-dimethyl-formamide at 0 - 20℃; Stage #2: methyl iodide In N,N-dimethyl-formamide at 20℃;	100%
Stage #1: 5-bromo-1H-pyrrolo[2,3-b]pyridine With sodium hydride In N,N-dimethyl-formamide at 0℃; for 0.5h; Inert atmosphere; Stage #2: methyl iodide In N,N-dimethyl-formamide at 25℃; for 3h; Inert atmosphere;	99%
Stage #1: 5-bromo-1H-pyrrolo[2,3-b]pyridine With sodium hydride In N,N-dimethyl acetamide; mineral oil at 20℃; for 0.5h; Stage #2: methyl iodide In N,N-dimethyl acetamide; mineral oil for 4h;	97%

: 183208-35-7
5-bromo-1H-pyrrolo[2,3-b]pyridine

: 757978-18-0
3-iodo-5-bromo-1H-pyrrolo[2,3-b]-pyridine

Conditions

Conditions	Yield
With N-iodo-succinimide In acetone at 20℃; for 0.333333h;	100%
Stage #1: 5-bromo-1H-pyrrolo[2,3-b]pyridine With potassium hydroxide In dichloromethane at 20℃; for 0.5h; Stage #2: With N-iodo-succinimide In dichloromethane for 15h;	100%
With N-iodo-succinimide In acetone at 20℃; for 0.333333h;	100%

: 76-02-8
Trichloroacetyl chloride

: 183208-35-7
5-bromo-1H-pyrrolo[2,3-b]pyridine

: 1-(5-bromo-1H-pyrrolo[2,3-b]pyridin-3-yl)-2,2,2-trichloroethanone

Conditions

Conditions	Yield
Stage #1: 5-bromo-1H-pyrrolo[2,3-b]pyridine With aluminum (III) chloride In dichloromethane at 20℃; for 0.166667h; Stage #2: trifluoroacetyl chloride In dichloromethane at 20℃;	100%
Stage #1: 5-bromo-1H-pyrrolo[2,3-b]pyridine With aluminum (III) chloride In dichloromethane at 0℃; for 3h; Stage #2: trifluoroacetyl chloride In dichloromethane at 25℃; for 16h;	72%
With aluminum (III) chloride In dichloromethane at 20℃;
Stage #1: 5-bromo-1H-pyrrolo[2,3-b]pyridine With aluminum (III) chloride at 20℃; for 0.166667h; Inert atmosphere; Stage #2: trifluoroacetyl chloride for 14h;	16.36 g
Stage #1: 5-bromo-1H-pyrrolo[2,3-b]pyridine With aluminum (III) chloride In dichloromethane at 0℃; for 3h; Stage #2: trifluoroacetyl chloride In dichloromethane at 25℃; for 16h;

: 76513-69-4
(2-trimethylethylsilylethoxy)methyl chloride

: 183208-35-7
5-bromo-1H-pyrrolo[2,3-b]pyridine

: 5-bromo-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrrolo[2,3-b]pyridine

Conditions

Conditions	Yield
Stage #1: 5-bromo-1H-pyrrolo[2,3-b]pyridine With sodium hydride In N,N-dimethyl-formamide; paraffin oil at 0 - 20℃; for 0.5h; Inert atmosphere; Stage #2: (2-trimethylethylsilylethoxy)methyl chloride In N,N-dimethyl-formamide; paraffin oil at 0 - 20℃;	100%
Stage #1: 5-bromo-1H-pyrrolo[2,3-b]pyridine With sodium hydride In N,N-dimethyl-formamide at -40℃; for 1h; Stage #2: (2-trimethylethylsilylethoxy)methyl chloride In N,N-dimethyl-formamide at -40℃; for 2h;	87%
Stage #1: 5-bromo-1H-pyrrolo[2,3-b]pyridine With sodium hydride In tetrahydrofuran at 0℃; for 0.5h; Inert atmosphere; Stage #2: (2-trimethylethylsilylethoxy)methyl chloride In tetrahydrofuran at 20℃; for 2h; Inert atmosphere;	79%

: 22118-09-8
2-bromoacetyl chloride

: 183208-35-7
5-bromo-1H-pyrrolo[2,3-b]pyridine

: 875639-57-9
2-bromo-1-(5-bromo-1H-pyrrolo[2,3-b]pyridin-3-yl)ethanone

Conditions

Conditions	Yield
Stage #1: 5-bromo-1H-pyrrolo[2,3-b]pyridine With aluminum (III) chloride In dichloromethane for 0.5h; Stage #2: 2-bromoacetyl chloride In dichloromethane for 2h;	100%
Stage #1: 5-bromo-1H-pyrrolo[2,3-b]pyridine With aluminum (III) chloride In dichloromethane at 20℃; for 1h; Stage #2: 2-bromoacetyl chloride In dichloromethane at 20℃;	92%
Stage #1: 5-bromo-1H-pyrrolo[2,3-b]pyridine With aluminum (III) chloride In dichloromethane for 0.5h; Inert atmosphere; Stage #2: 2-bromoacetyl chloride In dichloromethane for 2h;	138 mg

: 183208-35-7
5-bromo-1H-pyrrolo[2,3-b]pyridine

: 98-80-6
phenylboronic acid

: 611205-38-0
5-phenyl-1H-pyrrolo[2,3-b]pyridine

Conditions

Conditions	Yield
With potassium carbonate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride In 1,4-dioxane; water at 80℃; for 22.5h; Suzuki Coupling;	99%
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium carbonate In 1,4-dioxane; water at 80℃; for 22.5h; Suzuki coupling;	99%
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium carbonate In 1,4-dioxane; water at 80℃; for 22.5h; Inert atmosphere;	99%
With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium carbonate In 1,4-dioxane; water at 80℃; for 48h; Inert atmosphere;	82%
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In ethanol; toluene at 120℃; for 24h; Suzuki-Miyaura Coupling; Inert atmosphere;	62.93%

: 2516-47-4
cyclopropanemethylamine

: 183208-35-7
5-bromo-1H-pyrrolo[2,3-b]pyridine

: 1248587-76-9
N-(cyclopropylmethyl)-1H-pyrrolo[2,3-b]pyridin-5-amine

Conditions

Conditions	Yield
With dicyclohexyl-(2′,4′,6′-triisopropyl-3,6-dimethoxy-[1,1′-biphenyl]-2-yl)phosphine; chloro[2-(dicyclohexylphosphino)-3,6-dimethoxy-2’,4’,6’-triisopropyl-1,1’-biphenyl] [2-(2-aminoethyl)phenyl]palladium(II); lithium hexamethyldisilazane In tetrahydrofuran at 65℃; for 4h; Inert atmosphere; Sealed vial;	99%

: 7051-34-5
cyclopropylcarbinyl bromide

: 183208-35-7
5-bromo-1H-pyrrolo[2,3-b]pyridine

Conditions

Conditions	Yield
Stage #1: 5-bromo-1H-pyrrolo[2,3-b]pyridine With sodium hydride In N,N-dimethyl-formamide; mineral oil at 0℃; for 0.25h; Stage #2: cyclopropylcarbinyl bromide In N,N-dimethyl-formamide; mineral oil at 0 - 20℃; for 2h;	99%

: 100-39-0
benzyl bromide

: 183208-35-7
5-bromo-1H-pyrrolo[2,3-b]pyridine

: 1-benzyl-5-bromo-1H-pyrrolo[2,3-b] pyridine

Conditions

Conditions	Yield
With tetra(n-butyl)ammonium hydrogensulfate; potassium hydroxide In acetone at 75℃; Inert atmosphere;	99%
Stage #1: 5-bromo-1H-pyrrolo[2,3-b]pyridine With potassium tert-butylate In N,N-dimethyl acetamide for 0.25h; Cooling with ice; Stage #2: benzyl bromide In N,N-dimethyl acetamide at 20℃; for 1h; Cooling with ice;	0.45 g

: 542-69-8
1-iodo-butane

: 183208-35-7
5-bromo-1H-pyrrolo[2,3-b]pyridine

: 5-bromo-1-butyl-1H-pyrrolo[2,3-b]pyridine

Conditions

Conditions	Yield
With tetra(n-butyl)ammonium hydrogensulfate; potassium hydroxide In acetone at 75℃; Inert atmosphere;	99%

: 110-89-4
piperidine

: 201230-82-2
carbon monoxide

: 183208-35-7
5-bromo-1H-pyrrolo[2,3-b]pyridine

: C13H15N3O

Conditions

Conditions	Yield
With 2,2,6,6-tetramethyl-piperidine; dicobalt octacarbonyl In tert-Amyl alcohol under 1520.1 Torr; for 48h; Irradiation;	99%

...Expand

: 808144-32-3
(2,3-difluorophenyl)acetyl chloride

: 183208-35-7
5-bromo-1H-pyrrolo[2,3-b]pyridine

: 849069-12-1
1-(5-bromo-1H-pyrrolo[2,3-b]pyridin-3-yl)-2-(2,3-difluoro-phenyl)-ethanone

Conditions

Conditions	Yield
With aluminum (III) chloride In dichloromethane at 0 - 20℃; for 1.5h;	98%

: 75-36-5
acetyl chloride

: 183208-35-7
5-bromo-1H-pyrrolo[2,3-b]pyridine

: 866545-96-2
1-(5-bromo-1H-pyrrolo[2,3-b]pyridin-3-yl)ethanone

Conditions

Conditions	Yield
With aluminum (III) chloride In dichloromethane at 20℃; Friedel Crafts acylation; Inert atmosphere;	98%
aluminum (III) chloride In dichloromethane at 20℃; for 6h;	93%
Stage #1: 5-bromo-1H-pyrrolo[2,3-b]pyridine With aluminum (III) chloride In dichloromethane at 20℃; for 1h; Stage #2: acetyl chloride In dichloromethane for 5h;	93%

: 13154-24-0
triisopropylsilyl chloride

: 183208-35-7
5-bromo-1H-pyrrolo[2,3-b]pyridine

: 858116-66-2
5-bromo-1-(triisopropylsilyl)-1H-pyrrolo[2,3-b]pyridine

Conditions

Conditions	Yield
Stage #1: 5-bromo-1H-pyrrolo[2,3-b]pyridine With sodium hydride In 1,4-dioxane; N,N-dimethyl-formamide for 0.5h; Stage #2: triisopropylsilyl chloride In 1,4-dioxane; N,N-dimethyl-formamide at 20℃;	97%
Stage #1: 5-bromo-1H-pyrrolo[2,3-b]pyridine With sodium hydride In tetrahydrofuran at 0℃; for 0.25h; Schlenk technique; Inert atmosphere; Stage #2: triisopropylsilyl chloride In tetrahydrofuran at 0 - 20℃; Schlenk technique; Inert atmosphere;	94%
With potassium tert-butylate In tetrahydrofuran; N,N-dimethyl-formamide at 0 - 5℃; Solvent;	93.8%

: 106-94-5
propyl bromide

: 183208-35-7
5-bromo-1H-pyrrolo[2,3-b]pyridine

: 1440956-68-2
5-bromo-1-propyl-1H-pyrrolo[2,3-b]pyridine

Conditions

Conditions	Yield
With sodium hydride In N,N-dimethyl acetamide at 20℃; for 2.5h;	97%
Stage #1: 5-bromo-1H-pyrrolo[2,3-b]pyridine With sodium hydride In N,N-dimethyl acetamide; mineral oil at 20℃; for 0.5h; Stage #2: propyl bromide In N,N-dimethyl acetamide; mineral oil for 2h;	97%

: 73183-34-3
bis(pinacol)diborane

: 183208-35-7
5-bromo-1H-pyrrolo[2,3-b]pyridine

: 754214-56-7
5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrrolo[2,3-b]pyridine

Conditions

Conditions	Yield
With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium acetate In 1,4-dioxane at 80℃; Inert atmosphere;	95.9%
With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium acetate In 1,4-dioxane at 80℃; Inert atmosphere;	95.9%
With potassium acetate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 In 1,4-dioxane at 80℃; for 10h;	94.2%

: 589-08-2
N-Methyl-N-phenethylamine

: 183208-35-7
5-bromo-1H-pyrrolo[2,3-b]pyridine

: 1248587-68-9
N-methyl-N-phenethyl-1H-pyrrolo[2,3-b]pyridin-5-amine

Conditions

Conditions	Yield
With RuPhos palladacycle; lithium hexamethyldisilazane; ruphos In tetrahydrofuran at 65℃; for 4h; Inert atmosphere; Sealed vial;	95%

5-Bromo-7-azaindole Chemical Properties

Empirical Formula: C₇H₅BrN₂
Molecular Weight: 197.032
Nominal Mass: 196 Da
Average Mass: 197.032 Da
Monoisotopic Mass: 195.963603 Da
Index of Refraction: 1.727
Molar Refractivity: 44.3 cm³
Molar Volume: 111.2 cm³
Polarizability: 17.56 10-24cm³
Surface Tension: 64.4 dyne/cm
Density: 1.77 g/cm³
Melting point: 178.0-178.8 °C
Structure of 5-Bromo-1H-pyrrolo[2,3-b]pyridine (CAS NO.183208-35-7):

IUPAC Name: 5-Bromo-1H-pyrrolo[2,3-b]pyridine
Canonical SMILES: C1=CNC2=NC=C(C=C21)Br
InChI: InChI=1S/C7H5BrN2/c8-6-3-5-1-2-9-7(5)10-4-6/h1-4H,(H,9,10)
InChIKey: LPTVWZSQAIDCEB-UHFFFAOYSA-N
Product Category of 5-Bromo-1H-pyrrolo[2,3-b]pyridine (CAS NO.183208-35-7): Heterocycles;pyridine

5-Bromo-7-azaindole Safety Profile

Hazard Codes of 5-Bromo-1H-pyrrolo[2,3-b]pyridine (CAS NO.183208-35-7): Irritant Xi, Harmful Xn
Risk Statements: 22-41
R22:Harmful if swallowed.
R41:Risk of serious damage to the eyes.
Safety Statements: 26-39
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
S39:Wear eye / face protection.

5-Bromo-7-azaindole Specification

5-Bromo-1H-pyrrolo[2,3-b]pyridine , its cas register number is 183208-35-7. It also can be called 5-Bromo-7-azaindole ; and 3-Bromo-5,7-diazabicyclo[4.3.0]nona-1,3,5,8-tetraene .

Product Name

5-Bromo-7-azaindole

Synthetic route

5-Bromo-7-azaindole Chemical Properties

5-Bromo-7-azaindole Safety Profile

5-Bromo-7-azaindole Specification

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