5-(4-Chlorophenyl)-1H-pyrrolo[2,3-b]pyridine supplier

Name
1H-Pyrrolo[2,3-b]pyridine, 5-(4-chlorophenyl)-
EINECS
CAS No. 918516-27-5
Article Data14
CAS DataBase
Density 1.3±0.1 g/cm³
Solubility
Melting Point
Formula C₁₃H₉ClN₂
Boiling Point
Molecular Weight 228.681
Flash Point
Transport Information
Appearance
Safety
Risk Codes
Molecular Structure
Hazard Symbols
Synonyms 5-(4-chlorophenyl)-1H-pyrrolo[2,3-b]pyridine; 5-(4-chlorophenyl)-1h-pyrrolo(2,3-b)pyridine
PSA 28.68000
LogP 3.88330

Synthetic route

: 1679-18-1
4-Chlorophenylboronic acid

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

: 918516-27-5
5-(4-chlorophenyl)-1H-pyrrolo[2,3-b]pyridine

Conditions

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In Dimethyl ether; water Solvent; Temperature; Reflux;	92%
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In 1,2-dimethoxyethane; water Reflux;	92%
With bis-triphenylphosphine-palladium(II) chloride; potassium carbonate In 1,2-dimethoxyethane at 130℃; for 0.5h; Suzuki coupling; Inert atmosphere; Microwave irradiation;	76%

: 5-(4-chlorophenyl)-1H-pyrrolo[2,3-b]pyridine-3-carboxylic acid

: 918516-27-5
5-(4-chlorophenyl)-1H-pyrrolo[2,3-b]pyridine

Conditions

Conditions	Yield
With sodium hydroxide In water; N,N-dimethyl-formamide at 100℃; for 10h;	81.3%

: 1356397-48-2
5-(4-Cl-phenyl)azaindole

: 918516-27-5
5-(4-chlorophenyl)-1H-pyrrolo[2,3-b]pyridine

Conditions

Conditions	Yield
With potassium tert-butylate In 1-methyl-pyrrolidin-2-one at 20 - 120℃; for 2h; Product distribution / selectivity;	80%
With potassium tert-butylate In 1-methyl-pyrrolidin-2-one at 20 - 120℃; for 2h;

: 866546-07-8
5-chloro-1H-pyrrolo[2,3-b]pyridine

: 98-80-6
phenylboronic acid

: 918516-27-5
5-(4-chlorophenyl)-1H-pyrrolo[2,3-b]pyridine

Conditions

Conditions	Yield
With 1,1'-bis-(diphenylphosphino)ferrocene; palladium diacetate; caesium carbonate In water; toluene Inert atmosphere; Reflux;	75%

: 1431663-20-5
C14H9ClN2O2

: 918516-27-5
5-(4-chlorophenyl)-1H-pyrrolo[2,3-b]pyridine

Conditions

Conditions	Yield
With quinoline; copper chromite at 220℃; for 0.2h; Microwave irradiation;	58%

: 2-azido-3-(5-(4-chlorophenyl)pyridine-3-yl)acrylic acid

: 918516-27-5
5-(4-chlorophenyl)-1H-pyrrolo[2,3-b]pyridine

Conditions

Conditions	Yield
With quinoline; copper chromite at 220℃; for 0.2h; Microwave irradiation;	43%

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

: 918516-27-5
5-(4-chlorophenyl)-1H-pyrrolo[2,3-b]pyridine

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1: sodium carbonate / dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)CH2Cl2; palladium diacetate / 1,4-dioxane; water / 1.5 h / 90 °C 2: trifluoroacetic acid; N-iodo-succinimide / N,N-dimethyl-formamide / 2.5 h / 80 °C 3: lithium hydroxide / dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)CH2Cl2 / N,N-dimethyl-formamide / 18 h / 70 °C / Inert atmosphere 4: hydrogenchloride / water / 1 h / 50 °C / Inert atmosphere View Scheme
Multi-step reaction with 4 steps 1: sodium carbonate / dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; palladium diacetate / 1,4-dioxane; water / 1.5 h / 90 °C 2: N-Bromosuccinimide / N,N-dimethyl-formamide / 1 h / 20 °C 3: N,N,N',N'-tetramethylguanidine; copper(l) iodide / bis-triphenylphosphine-palladium(II) chloride / toluene / 2 h / 100 °C / Inert atmosphere 4: potassium tert-butylate / 1-methyl-pyrrolidin-2-one / 2 h / 20 - 120 °C View Scheme
Multi-step reaction with 4 steps 1: sodium carbonate / dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)CH2Cl2; palladium diacetate / 1,4-dioxane; water / 1.5 h / 90 °C 2: N-Bromosuccinimide / N,N-dimethyl-formamide / 1 h / 20 °C 3: lithium hydroxide / dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)CH2Cl2 / N,N-dimethyl-formamide / 18 h / 70 °C 4: hydrogenchloride / water / 1 h / 50 °C / Inert atmosphere View Scheme

: 1679-18-1
4-Chlorophenylboronic acid

: 918516-27-5
5-(4-chlorophenyl)-1H-pyrrolo[2,3-b]pyridine

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1: sodium carbonate / dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)CH2Cl2; palladium diacetate / 1,4-dioxane; water / 1.5 h / 90 °C 2: trifluoroacetic acid; N-iodo-succinimide / N,N-dimethyl-formamide / 2.5 h / 80 °C 3: lithium hydroxide / dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)CH2Cl2 / N,N-dimethyl-formamide / 18 h / 70 °C / Inert atmosphere 4: hydrogenchloride / water / 1 h / 50 °C / Inert atmosphere View Scheme
Multi-step reaction with 4 steps 1: sodium carbonate / dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; palladium diacetate / 1,4-dioxane; water / 1.5 h / 90 °C 2: N-Bromosuccinimide / N,N-dimethyl-formamide / 1 h / 20 °C 3: N,N,N',N'-tetramethylguanidine; copper(l) iodide / bis-triphenylphosphine-palladium(II) chloride / toluene / 2 h / 100 °C / Inert atmosphere 4: potassium tert-butylate / 1-methyl-pyrrolidin-2-one / 2 h / 20 - 120 °C View Scheme
Multi-step reaction with 4 steps 1: sodium carbonate / dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)CH2Cl2; palladium diacetate / 1,4-dioxane; water / 1.5 h / 90 °C 2: N-Bromosuccinimide / N,N-dimethyl-formamide / 1 h / 20 °C 3: lithium hydroxide / dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)CH2Cl2 / N,N-dimethyl-formamide / 18 h / 70 °C 4: hydrogenchloride / water / 1 h / 50 °C / Inert atmosphere View Scheme

: 84596-08-7
5-(4-chlorophenyl)pyridin-2-ylamine

: 918516-27-5
5-(4-chlorophenyl)-1H-pyrrolo[2,3-b]pyridine

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: trifluoroacetic acid; N-iodo-succinimide / N,N-dimethyl-formamide / 2.5 h / 80 °C 2: lithium hydroxide / dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 / N,N-dimethyl-formamide / 18 h / 70 °C / Inert atmosphere 3: hydrogenchloride / water / 1 h / 50 °C / Inert atmosphere View Scheme
Multi-step reaction with 3 steps 1: N-Bromosuccinimide / N,N-dimethyl-formamide / 1 h / 20 °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 / Inert atmosphere View Scheme
Multi-step reaction with 3 steps 1: trifluoroacetic acid; N-iodo-succinimide / N,N-dimethyl-formamide / 2.5 h / 80 °C 2: lithium hydroxide / dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 / 1,4-dioxane; water / 24 h / 80 °C 3: hydrogenchloride / water / 1 h / 50 °C / Inert atmosphere View Scheme

: 911113-60-5
C11H8BrClN2

: 918516-27-5
5-(4-chlorophenyl)-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 / Inert atmosphere View Scheme
Multi-step reaction with 2 steps 1: N,N,N',N'-tetramethylguanidine; copper(l) iodide / bis-triphenylphosphine-palladium(II) chloride / toluene / 2 h / 100 °C / Inert atmosphere 2: potassium tert-butylate / 1-methyl-pyrrolidin-2-one / 2 h / 20 - 120 °C View Scheme
Multi-step reaction with 2 steps 1: N,N,N',N'-tetramethylguanidine / copper(l) iodide; bis-triphenylphosphine-palladium(II) chloride / toluene / 2 h / 100 °C / Inert atmosphere 2: potassium tert-butylate / 1-methyl-pyrrolidin-2-one / 2 h / 20 - 120 °C View Scheme
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 / N,N-dimethyl-formamide; water / 1 h / 50 °C View Scheme

: 1356397-47-1
C15H15ClN2O

: 918516-27-5
5-(4-chlorophenyl)-1H-pyrrolo[2,3-b]pyridine

Conditions

Conditions	Yield
With hydrogenchloride In water at 50℃; for 1h; Product distribution / selectivity; Inert atmosphere;
With hydrogenchloride In water; N,N-dimethyl-formamide at 50℃; for 1h;

: 1356397-46-0
C11H8ClIN2

: 918516-27-5
5-(4-chlorophenyl)-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 / Inert atmosphere 2: hydrogenchloride / water / 1 h / 50 °C / Inert atmosphere View Scheme
Multi-step reaction with 2 steps 1: lithium hydroxide / dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 / 1,4-dioxane; water / 24 h / 80 °C 2: hydrogenchloride / water / 1 h / 50 °C / Inert atmosphere View Scheme
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 / Inert atmosphere 2: hydrogenchloride / N,N-dimethyl-formamide; water / 1 h / 50 °C View Scheme
Multi-step reaction with 2 steps 1: lithium hydroxide / dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 / 1,4-dioxane; water / 24 h / 80 °C 2: hydrogenchloride / N,N-dimethyl-formamide; water / 1 h / 50 °C View Scheme

: C11H9ClN2*(x)ClH

: 918516-27-5
5-(4-chlorophenyl)-1H-pyrrolo[2,3-b]pyridine

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1: sodium hydroxide / water 2: N-Bromosuccinimide / N,N-dimethyl-formamide / 1 h / 20 °C 3: N,N,N',N'-tetramethylguanidine / copper(l) iodide; bis-triphenylphosphine-palladium(II) chloride / toluene / 2 h / 100 °C / Inert atmosphere 4: potassium tert-butylate / 1-methyl-pyrrolidin-2-one / 2 h / 20 - 120 °C View Scheme
Multi-step reaction with 4 steps 1: sodium hydroxide / water 2: N-Bromosuccinimide / N,N-dimethyl-formamide / 1 h / 20 °C 3: lithium hydroxide / dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 / N,N-dimethyl-formamide / 18 h / 70 °C 4: hydrogenchloride / N,N-dimethyl-formamide; water / 1 h / 50 °C View Scheme
Multi-step reaction with 4 steps 1: sodium hydroxide / water 2: trifluoroacetic acid; N-iodo-succinimide / N,N-dimethyl-formamide / 2.5 h / 80 °C 3: lithium hydroxide / dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 / N,N-dimethyl-formamide / 18 h / 70 °C / Inert atmosphere 4: hydrogenchloride / N,N-dimethyl-formamide; water / 1 h / 50 °C View Scheme
Multi-step reaction with 4 steps 1: sodium hydroxide / water 2: trifluoroacetic acid; N-iodo-succinimide / N,N-dimethyl-formamide / 2.5 h / 80 °C 3: lithium hydroxide / dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 / 1,4-dioxane; water / 24 h / 80 °C 4: hydrogenchloride / N,N-dimethyl-formamide; water / 1 h / 50 °C View Scheme

: C15H11ClN4O2

: 918516-27-5
5-(4-chlorophenyl)-1H-pyrrolo[2,3-b]pyridine

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: lithium hydroxide / tetrahydrofuran 2: quinoline; copper chromite / 0.2 h / 220 °C / Microwave irradiation View Scheme
Multi-step reaction with 3 steps 1: toluene / 0.2 h / 200 °C / Microwave irradiation 2: lithium hydroxide / tetrahydrofuran 3: quinoline; copper chromite / 0.2 h / 220 °C / Microwave irradiation View Scheme

: 1426575-26-9
methyl 5-(4-chlorophenyl)-1H-pyrrolo[2,3-b]pyridine-2-carboxylate

: 918516-27-5
5-(4-chlorophenyl)-1H-pyrrolo[2,3-b]pyridine

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: lithium hydroxide / tetrahydrofuran 2: quinoline; copper chromite / 0.2 h / 220 °C / Microwave irradiation View Scheme

: 195062-61-4
4-chlorophenylboronic acid pinacol ester

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

: 918516-27-5
5-(4-chlorophenyl)-1H-pyrrolo[2,3-b]pyridine

Conditions

Conditions	Yield
With sodium carbonate In water at 120℃; for 0.5h; Irradiation;	19 mg

: 106-39-8
bromochlorobenzene

: 918516-27-5
5-(4-chlorophenyl)-1H-pyrrolo[2,3-b]pyridine

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: potassium acetate; tetrakis(triphenylphosphine) palladium(0) / 1,4-dioxane / 0.75 h / 120 °C / Irradiation 2: sodium carbonate / water / 0.5 h / 120 °C / Irradiation View Scheme

: 1372929-27-5
5-bromo-1-(tert-butyl)-1H-pyrrolo[2,3-b]pyridine-3-carbonitrile

: 918516-27-5
5-(4-chlorophenyl)-1H-pyrrolo[2,3-b]pyridine

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1: dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; sodium carbonate / toluene; water / 7 h / 85 °C / Inert atmosphere 2: aluminum (III) chloride / chlorobenzene / 100 °C / Inert atmosphere 3: hydrogen bromide; water / 24 h / 100 °C 4: sodium hydroxide / water; dimethyl sulfoxide / 24 h / 113 - 115 °C View Scheme

: 1418299-52-1
5-(4-chlorophenyl)-1-(tert-butyl)-1H-pyrrolo[2,3-b]pyridine-3-carbonitrile

: 918516-27-5
5-(4-chlorophenyl)-1H-pyrrolo[2,3-b]pyridine

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: aluminum (III) chloride / chlorobenzene / 100 °C / Inert atmosphere 2: hydrogen bromide; water / 24 h / 100 °C 3: sodium hydroxide / water; dimethyl sulfoxide / 24 h / 113 - 115 °C View Scheme

: 1878-66-6
4-chlorophenylacetic Acid

: 918516-27-5
5-(4-chlorophenyl)-1H-pyrrolo[2,3-b]pyridine

Conditions

Conditions	Yield
Multi-step reaction with 5 steps 1.1: trichlorophosphate / 8 h / 70 °C 1.2: 2 h / 10 - 26 °C 2.1: sodium methylate / methanol; dimethyl sulfoxide / 1 h / 100 °C / Inert atmosphere 3.1: aluminum (III) chloride / chlorobenzene / 100 °C / Inert atmosphere 4.1: hydrogen bromide; water / 24 h / 100 °C 5.1: sodium hydroxide / water; dimethyl sulfoxide / 24 h / 113 - 115 °C View Scheme
Multi-step reaction with 5 steps 1.1: trichlorophosphate / 2.75 h / 10 - 85 °C / Inert atmosphere 1.2: 1.5 h / 0 - 5 °C 2.1: caesium carbonate / dimethyl sulfoxide / 1.5 h / 80 °C / Inert atmosphere 3.1: aluminum (III) chloride / chlorobenzene / 100 °C / Inert atmosphere 4.1: hydrogen bromide; water / 24 h / 100 °C 5.1: sodium hydroxide / water; dimethyl sulfoxide / 24 h / 113 - 115 °C View Scheme

Yield

Multi-step reaction with 5 steps
1.1: trichlorophosphate / 8 h / 70 °C
1.2: 2 h / 10 - 26 °C
2.1: sodium methylate / methanol; dimethyl sulfoxide / 1 h / 100 °C / Inert atmosphere
3.1: aluminum (III) chloride / chlorobenzene / 100 °C / Inert atmosphere
4.1: hydrogen bromide; water / 24 h / 100 °C
5.1: sodium hydroxide / water; dimethyl sulfoxide / 24 h / 113 - 115 °C
View Scheme

Multi-step reaction with 5 steps
1.1: trichlorophosphate / 2.75 h / 10 - 85 °C / Inert atmosphere
1.2: 1.5 h / 0 - 5 °C
2.1: caesium carbonate / dimethyl sulfoxide / 1.5 h / 80 °C / Inert atmosphere
3.1: aluminum (III) chloride / chlorobenzene / 100 °C / Inert atmosphere
4.1: hydrogen bromide; water / 24 h / 100 °C
5.1: sodium hydroxide / water; dimethyl sulfoxide / 24 h / 113 - 115 °C
View Scheme

: N-(2-(4-chlorophenyl)-3-(dimethylamino)allylidene)-N-methylmethanaminium hexafluorophosphate

: 918516-27-5
5-(4-chlorophenyl)-1H-pyrrolo[2,3-b]pyridine

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1: sodium methylate / methanol; dimethyl sulfoxide / 1 h / 100 °C / Inert atmosphere 2: aluminum (III) chloride / chlorobenzene / 100 °C / Inert atmosphere 3: hydrogen bromide; water / 24 h / 100 °C 4: sodium hydroxide / water; dimethyl sulfoxide / 24 h / 113 - 115 °C View Scheme

: N-(2-(4-chlorophenyl)-3-(dimethylamino)allylidene)-N-methylmethanaminium tetrafluoroborate

: 918516-27-5
5-(4-chlorophenyl)-1H-pyrrolo[2,3-b]pyridine

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1: caesium carbonate / dimethyl sulfoxide / 1.5 h / 80 °C / Inert atmosphere 2: aluminum (III) chloride / chlorobenzene / 100 °C / Inert atmosphere 3: hydrogen bromide; water / 24 h / 100 °C 4: sodium hydroxide / water; dimethyl sulfoxide / 24 h / 113 - 115 °C View Scheme

: 5-(4-chlorophenyl)-1H-pyrrolo[2,3-b]pyridine-3-carbonitrile

: 918516-27-5
5-(4-chlorophenyl)-1H-pyrrolo[2,3-b]pyridine

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: hydrogen bromide; water / 24 h / 100 °C 2: sodium hydroxide / water; dimethyl sulfoxide / 24 h / 113 - 115 °C View Scheme

: 5-(4-chlorophenyl)-1H-pyrrolo[2,3-b]pyridine-3-carboxylic acid hydrobromide

: 918516-27-5
5-(4-chlorophenyl)-1H-pyrrolo[2,3-b]pyridine

Conditions

Conditions	Yield
With sodium hydroxide In water; dimethyl sulfoxide at 113 - 115℃; for 24h;	31.8 g

: 918516-27-5
5-(4-chlorophenyl)-1H-pyrrolo[2,3-b]pyridine

: 1103234-56-5
2,6-difluoro-3-(propane-1-sulfonylamino)benzoic acid

: vemurafenib

Conditions

Conditions	Yield
Stage #1: 2,6-difluoro-3-(propane-1-sulfonylamino)benzoic acid With oxalyl dichloride; N,N-dimethyl-formamide In dichloromethane at 20℃; for 2.5h; Stage #2: 5-(4-chlorophenyl)-1H-pyrrolo[2,3-b]pyridine; aluminum (III) chloride In dichloromethane at 20℃; for 3h;	85%
Stage #1: 2,6-difluoro-3-(propane-1-sulfonylamino)benzoic acid With oxalyl dichloride In dichloromethane at 18 - 26℃; for 2h; Stage #2: 5-(4-chlorophenyl)-1H-pyrrolo[2,3-b]pyridine With aluminum (III) chloride In dichloromethane at 0 - 26℃; for 5h;	70%

: 918516-27-5
5-(4-chlorophenyl)-1H-pyrrolo[2,3-b]pyridine

: 2-methyl-5-(propylsulfonamido)benzoic acid

: N-(3-(5-(4-chlorophenyl)-1H-pyrrolo[2,3-b]pyridine-3-carbonyl)-4-methylphenyl)propane-1-sulfonamide

Conditions

Conditions	Yield
Stage #1: 2-methyl-5-(propylsulfonamido)benzoic acid With oxalyl dichloride; N,N-dimethyl-formamide In dichloromethane Stage #2: 5-(4-chlorophenyl)-1H-pyrrolo[2,3-b]pyridine With aluminum (III) chloride	80%

: 918516-27-5
5-(4-chlorophenyl)-1H-pyrrolo[2,3-b]pyridine

: 98-88-4
benzoyl chloride

: 1426575-27-0
C20H13ClN2O

Conditions

Conditions	Yield
With zirconium(IV) chloride Friedel-Crafts Acylation;	79%

: 918516-27-5
5-(4-chlorophenyl)-1H-pyrrolo[2,3-b]pyridine

: 918524-58-0
2-fluoro-5-(propylsulfonamido)benzoic acid

: N-(3-(5-(4-chlorophenyl)-1H-pyrrolo[2,3-b]pyridine-3-carbonyl)-4-fluorophenyl)propane-1-sulfonamide

Conditions

Conditions	Yield
Stage #1: 2-fluoro-5-(propylsulfonamido)benzoic acid With oxalyl dichloride; N,N-dimethyl-formamide In dichloromethane Stage #2: 5-(4-chlorophenyl)-1H-pyrrolo[2,3-b]pyridine With aluminum (III) chloride	71%
Stage #1: 2-fluoro-5-(propylsulfonamido)benzoic acid With oxalyl dichloride; N,N-dimethyl-formamide In dichloromethane Friedel-Crafts Acylation; Stage #2: 5-(4-chlorophenyl)-1H-pyrrolo[2,3-b]pyridine With aluminum (III) chloride In dichloromethane Friedel-Crafts Acylation;	71%

: 918516-27-5
5-(4-chlorophenyl)-1H-pyrrolo[2,3-b]pyridine

: 918523-49-6
2-fluoro-3-(propylsulfonamido)benzoic acid

: N-(3-(5-(4-chlorophenyl)-1H-pyrrolo[2,3-b]pyridine-3-carbonyl)-2-fluorophenyl)propane-1-sulfonamide

Conditions

Conditions	Yield
Stage #1: 2-fluoro-3-(propylsulfonamido)benzoic acid With oxalyl dichloride; N,N-dimethyl-formamide In dichloromethane Stage #2: 5-(4-chlorophenyl)-1H-pyrrolo[2,3-b]pyridine With aluminum (III) chloride	68%
Stage #1: 2-fluoro-3-(propylsulfonamido)benzoic acid With oxalyl dichloride; N,N-dimethyl-formamide In dichloromethane Friedel-Crafts Acylation; Stage #2: 5-(4-chlorophenyl)-1H-pyrrolo[2,3-b]pyridine With aluminum (III) chloride In dichloromethane Friedel-Crafts Acylation;	68%

: 918516-27-5
5-(4-chlorophenyl)-1H-pyrrolo[2,3-b]pyridine

: 918523-58-7
N-(2,4-difluoro-3-formylphenyl)propane-1-sulfonamide

: 1522361-91-6
N-(3-(bis(5-(4-chlorophenyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)methyl)-2,4-difluorophenyl)propane-1-sulfonamide

Conditions

Conditions	Yield
With potassium carbonate In methanol; water at 130℃; for 0.5h; Microwave irradiation;	64%

: 918516-27-5
5-(4-chlorophenyl)-1H-pyrrolo[2,3-b]pyridine

: 1186194-32-0
2,6-difluoro-3-(propylsulfonamido)benzoyl chloride

: vemurafenib

Conditions

Conditions	Yield
Stage #1: 5-(4-chlorophenyl)-1H-pyrrolo[2,3-b]pyridine With aluminum (III) chloride In 1,2-dichloro-ethane at 0℃; for 0.666667h; Stage #2: 2,6-difluoro-3-(propylsulfonamido)benzoyl chloride In 1,2-dichloro-ethane at 0 - 20℃;	60%
With aluminum (III) chloride In dichloromethane at 0 - 20℃; for 3h;

: 918516-27-5
5-(4-chlorophenyl)-1H-pyrrolo[2,3-b]pyridine

: 1186194-09-1
2,6-difluoro-3-(2-methylpropylsulfonamido)benzoic acid

: N-(3-(5-(4-chlorophenyl)-1H-pyrrolo[2,3-b]pyridine-3-carbonyl)-2,4-difluorophenyl)-2-methylpropane-1-sulfonamide

Conditions

Conditions	Yield
Stage #1: 5-(4-chlorophenyl)-1H-pyrrolo[2,3-b]pyridine; 2,6-difluoro-3-(2-methylpropylsulfonamido)benzoic acid With oxalyl dichloride; N,N-dimethyl-formamide In dichloromethane Stage #2: With aluminum (III) chloride In dichloromethane	58%

: 918516-27-5
5-(4-chlorophenyl)-1H-pyrrolo[2,3-b]pyridine

: 3-fluoro-5-(propylsulfonamido)benzoic acid

: N-(3-(5-(4-chlorophenyl)-1H-pyrrolo[2,3-b]pyridine-3-carbonyl)-5-fluorophenyl)propane-1-sulfonamide

Conditions

Conditions	Yield
Stage #1: 3-fluoro-5-(propylsulfonamido)benzoic acid With oxalyl dichloride; N,N-dimethyl-formamide In dichloromethane Friedel-Crafts Acylation; Stage #2: 5-(4-chlorophenyl)-1H-pyrrolo[2,3-b]pyridine With aluminum (III) chloride In dichloromethane Friedel-Crafts Acylation;	55%

: 918516-27-5
5-(4-chlorophenyl)-1H-pyrrolo[2,3-b]pyridine

: 2,6-difluoro-3-(pentylsulfonamido)benzoic acid

: N-(3-(5-(4-chlorophenyl)-1H-pyrrolo[2,3-b]pyridine-3-carbonyl)-2,4-difluorophenyl)pentane-1-sulfonamide

Conditions

Conditions	Yield
Stage #1: 2,6-difluoro-3-(pentylsulfonamido)benzoic acid With oxalyl dichloride; N,N-dimethyl-formamide In dichloromethane Stage #2: 5-(4-chlorophenyl)-1H-pyrrolo[2,3-b]pyridine With aluminum (III) chloride	54%

: 918516-27-5
5-(4-chlorophenyl)-1H-pyrrolo[2,3-b]pyridine

: 2-methyl-3-(propylsulfonamido)benzoic acid

: N-(3-(5-(4-chlorophenyl)-1H-pyrrolo[2,3-b]pyridine-3-carbonyl)-2-methylphenyl)propane-1-sulfonamide

Conditions

Conditions	Yield
Stage #1: 2-methyl-3-(propylsulfonamido)benzoic acid With oxalyl dichloride; N,N-dimethyl-formamide In dichloromethane Stage #2: 5-(4-chlorophenyl)-1H-pyrrolo[2,3-b]pyridine With aluminum (III) chloride	53%
Stage #1: 2-methyl-3-(propylsulfonamido)benzoic acid With oxalyl dichloride; N,N-dimethyl-formamide In dichloromethane Friedel-Crafts Acylation; Stage #2: 5-(4-chlorophenyl)-1H-pyrrolo[2,3-b]pyridine With aluminum (III) chloride In dichloromethane Friedel-Crafts Acylation;	53%

: 849409-82-1
3-(propylsulfonamido)benzoic acid

: 918516-27-5
5-(4-chlorophenyl)-1H-pyrrolo[2,3-b]pyridine

: N-(3-(5-(4-chlorophenyl)-1H-pyrrolo[2,3-b]pyridine-3-carbonyl)phenyl)-propane-1-sulfonamide

Conditions

Conditions	Yield
Stage #1: 3-(propylsulfonamido)benzoic acid With oxalyl dichloride; N,N-dimethyl-formamide In dichloromethane Friedel-Crafts Acylation; Stage #2: 5-(4-chlorophenyl)-1H-pyrrolo[2,3-b]pyridine With aluminum (III) chloride In dichloromethane Friedel-Crafts Acylation;	52%

: 918516-27-5
5-(4-chlorophenyl)-1H-pyrrolo[2,3-b]pyridine

: 2-chloro-3-(propylsulfonamido)benzoic acid

: N-(2-chloro-3-(5-(4-chlorophenyl)-1H-pyrrolo[2,3-b]pyridine-3-carbonyl)phenyl)propane-1-sulfonamide

Conditions

Conditions	Yield
Stage #1: 2-chloro-3-(propylsulfonamido)benzoic acid With oxalyl dichloride; N,N-dimethyl-formamide In dichloromethane Stage #2: 5-(4-chlorophenyl)-1H-pyrrolo[2,3-b]pyridine With aluminum (III) chloride	46%
Stage #1: 2-chloro-3-(propylsulfonamido)benzoic acid With oxalyl dichloride; N,N-dimethyl-formamide In dichloromethane Friedel-Crafts Acylation; Stage #2: 5-(4-chlorophenyl)-1H-pyrrolo[2,3-b]pyridine With aluminum (III) chloride In dichloromethane Friedel-Crafts Acylation;	46%

: 918516-27-5
5-(4-chlorophenyl)-1H-pyrrolo[2,3-b]pyridine

: 75-36-5
acetyl chloride

: 1-(5-(4-chlorophenyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)ethanone

Conditions

Conditions	Yield
Stage #1: 5-(4-chlorophenyl)-1H-pyrrolo[2,3-b]pyridine With aluminum (III) chloride In dichloromethane at 20℃; for 0.5h; Stage #2: acetyl chloride In dichloromethane at 20℃; for 12h; Stage #3: With sodium hydroxide In water pH=5;	42%

: 918516-27-5
5-(4-chlorophenyl)-1H-pyrrolo[2,3-b]pyridine

: C10H11BrClNO3S

: N-(3-bromo-5-(5-(4-chlorophenyl)-1H-pyrrolo[2,3-b]pyridine-3-carbonyl)phenyl)propane-1-sulfonamide

Conditions

Conditions	Yield
With aluminum (III) chloride In dichloromethane at 20℃;	38%

: 918516-27-5
5-(4-chlorophenyl)-1H-pyrrolo[2,3-b]pyridine

: C12H13F2NO3

: N-(3-(5-(4-chlorophenyl)-1H-pyrrolo[2,3-b]pyridine-3-carbonyl)-2,4-difluorophenyl)butyramide

Conditions

Conditions	Yield
Stage #1: C12H13F2NO3 With oxalyl dichloride; N,N-dimethyl-formamide In dichloromethane at 20℃; Stage #2: 5-(4-chlorophenyl)-1H-pyrrolo[2,3-b]pyridine With aluminum (III) chloride In dichloromethane at 20℃;	38%

: 918516-27-5
5-(4-chlorophenyl)-1H-pyrrolo[2,3-b]pyridine

: 4-fluoro-3-(propylsulfonamido)benzoic acid

: N-(5-(5-(4-chlorophenyl)-1H-pyrrolo[2,3-b]pyridine-3-carbonyl)-2-fluorophenyl)propane-1-sulfonamide

Conditions

Conditions	Yield
Stage #1: 4-fluoro-3-(propylsulfonamido)benzoic acid With oxalyl dichloride; N,N-dimethyl-formamide In dichloromethane Friedel-Crafts Acylation; Stage #2: 5-(4-chlorophenyl)-1H-pyrrolo[2,3-b]pyridine With aluminum (III) chloride In dichloromethane Friedel-Crafts Acylation;	37%

: 918516-27-5
5-(4-chlorophenyl)-1H-pyrrolo[2,3-b]pyridine

: 1186609-71-1
2,6-difluoro-3-(ethylsulfonamido)benzoic acid

: N-(3-(5-(4-chlorophenyl)-1H-pyrrolo[2,3-b]pyridine-3-carbonyl)-2,4-difluorophenyl)ethanesulfonamide

Conditions

Conditions	Yield
With aluminum (III) chloride; oxalyl dichloride; N,N-dimethyl-formamide In dichloromethane	29%

: 67-56-1
methanol

: 918516-27-5
5-(4-chlorophenyl)-1H-pyrrolo[2,3-b]pyridine

: 918523-58-7
N-(2,4-difluoro-3-formylphenyl)propane-1-sulfonamide

A: propane-1-sulfonic acid (3-{[5-(4-chloro-phenyl)-1H-pyrrolo[2,3-b]pyridin-3-yl]-methoxy-methyl}-2,4-difluoro-phenyl)-amide

B: propane-1-sulfonic acid (3-{[5-(4-chlorophenyl)-1H-pyrrolo[2,3-b]pyridine-3-yl]hydroxymethyl}-2,4-difluorophenyl)amide

Conditions

Conditions	Yield
With potassium hydroxide at 20℃; for 72h;
With potassium hydroxide at 20℃; for 72h;

...Expand

5-(4-Chlorophenyl)-1H-pyrrolo[2,3-b]pyridine Specification

The 5-(4-Chlorophenyl)-1H-pyrrolo[2,3-b]pyridine, with the CAS registry number 918516-27-5, is also known as 1H-Pyrrolo[2,3-b]pyridine, 5-(4-chlorophenyl)-. This chemical's molecular formula is C₁₃H₉ClN₂ and molecular weight is 228.68. What's more, its systematic name is 5-(4-Chlorophenyl)-1H-pyrrolo[2,3-b]pyridine.

Physical properties of 5-(4-Chlorophenyl)-1H-pyrrolo[2,3-b]pyridine are: (1)ACD/LogP: 4.03±0.32; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 4.02; (4)ACD/LogD (pH 7.4): 4.03; (5)ACD/BCF (pH 5.5): 659.06; (6)ACD/BCF (pH 7.4): 684.05; (7)ACD/KOC (pH 5.5): 3587.03; (8)ACD/KOC (pH 7.4): 3723.04; (9)#H bond acceptors: 2; (10)#H bond donors: 1; (11)#Freely Rotating Bonds: 1; (12)Polar Surface Area: 28.68 Å²; (13)Index of Refraction: 1.693; (14)Molar Refractivity: 66.1±0.3 cm³; (15)Molar Volume: 172.3±3.0 cm³; (16)Polarizability: 26.2±0.5×10^-24cm³; (17)Surface Tension: 57.3±3.0 dyne/cm; (18)Density: 1.3±0.1 g/cm³.

You can still convert the following datas into molecular structure:
(1)SMILES: c1cc(ccc1c2cc3cc[nH]c3nc2)Cl
(2)Std. InChI: InChI=1S/C13H9ClN2/c14-12-3-1-9(2-4-12)11-7-10-5-6-15-13(10)16-8-11/h1-8H,(H,15,16)
(3)Std. InChIKey: AIRHBAXIGSQPNX-UHFFFAOYSA-N

Product Name

1H-Pyrrolo[2,3-b]pyridine, 5-(4-chlorophenyl)-

Synthetic route

5-(4-Chlorophenyl)-1H-pyrrolo[2,3-b]pyridine Specification

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