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1-Methyl-1H-pyrrolo[2,3-b]pyridine

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1-Methyl-1H-pyrrolo[2,3-b]pyridine Basic information
Product Name:1-Methyl-1H-pyrrolo[2,3-b]pyridine
Synonyms:1-Methyl-1H-pyrrolo[2,3-b]pyridine;1-Methyl-7-azaindole;1H-Pyrrolo[2,3-b]pyridine, 1-Methyl-;1-Methylpyrrolo[2,3-b]pyridine
CAS:27257-15-4
MF:C8H8N2
MW:132.16
EINECS:
Product Categories:Azaindoles
Mol File:27257-15-4.mol
1-Methyl-1H-pyrrolo[2,3-b]pyridine Structure
1-Methyl-1H-pyrrolo[2,3-b]pyridine Chemical Properties
Boiling point 112-116 °C(Press: 21 Torr)
density 1.107 g/cm3(Temp: 22 °C)
storage temp. 2-8°C
pka5.35±0.30(Predicted)
AppearanceLight yellow to green yellow Liquid
Safety Information
HS Code 2933998090
MSDS Information
1-Methyl-1H-pyrrolo[2,3-b]pyridine Usage And Synthesis
UsesN-Methyl-d3-7-azaindole is a labeled reactant used in the preparation of blue fluorescent amino acids as in vivo building blocks for protein engineering.
Synthesis
7-Azaindole

271-63-6

Iodomethane

74-88-4

1-Methyl-1H-pyrrolo[2,3-b]pyridine

27257-15-4

GENERAL METHODS: Preparation of known compound 1a: 7-azaindole (2 g, 16.95 mmol) and anhydrous DMF (10 mL) were added to a dry round-bottomed flask equipped with a magnetic stirring bar under nitrogen atmosphere. The reaction mixture was cooled to 0 °C, 60% sodium hydride (1.2 eq.) was added in batches and stirring was continued for 1 h at this temperature. Subsequently, iodomethane (1.1 eq.) was added slowly and dropwise, keeping the reaction temperature at 0 °C and continuing to stir for 1 hour. Upon completion of the reaction, the reaction was quenched with ice-cold water (100 mL) and extracted with ethyl acetate (3 x 100 mL). The organic layers were combined, dried with anhydrous sodium sulfate, filtered and concentrated under reduced pressure to give 1-methyl-7-azaindole in quantitative yield.

References[1] Beilstein Journal of Organic Chemistry, 2016, vol. 12, p. 309 - 313
[2] Green Chemistry, 2017, vol. 19, # 23, p. 5559 - 5563
[3] Organic Letters, 2013, vol. 15, # 22, p. 5718 - 5721
[4] Chemical and Pharmaceutical Bulletin, 2007, vol. 55, # 2, p. 255 - 267
[5] Journal of Natural Products, 2009, vol. 72, # 12, p. 2199 - 2202
1-Methyl-1H-pyrrolo[2,3-b]pyridine Preparation Products And Raw materials
Raw materials7-Azaindole-->Iodomethane-->N,N-Dimethylformamide-->Sodium hydride
Tag:1-Methyl-1H-pyrrolo[2,3-b]pyridine(27257-15-4) Related Product Information
2-(tert-Butyl)-1-(2,4-dichlorobenzyl)-1H-pyrrolo[2,3-b]pyridine 2-(tert-Butyl)-1-methyl-1H-pyrrolo[2,3-b]pyridine IMPLITAPIDE N-[2-(2,4-Dimethyl-9H-pyrido[2,3-b]indol-9-yl)ethyl]-3-fluorobenzamide N-[2-(2,4-Dimethyl-9H-pyrido[2,3-b]indol-9-yl)ethyl]-3,4,5-trimethoxybenzamide 2-Chloro-N-[2-(2,4-dimethyl-9H-pyrido[2,3-b]indol-9-yl)ethyl]benzamide 1-[(2-Chloro-1,3-thiazol-5-yl)methyl]-1H-pyrrolo[2,3-b]pyridine 2-(tert-Butyl)-1-(4-methylbenzyl)-1H-pyrrolo[2,3-b]pyridine 2-(tert-Butyl)-1-(3-methylbenzyl)-1H-pyrrolo[2,3-b]pyridine 2-(tert-Butyl)-1-(3-fluorobenzyl)-1H-pyrrolo[2,3-b]pyridine N-[2-(2,4-Dimethyl-9H-pyrido[2,3-b]indol-9-yl)ethyl]-N'-(4-methylphenyl)thiourea N-(3-Chlorophenyl)-N'-[2-(2,4-dimethyl-9H-pyrido[2,3-b]indol-9-yl)ethyl]thiourea 1-Benzyl-2-(tert-butyl)-1H-pyrrolo[2,3-b]pyridine N-[2-(2,4-Dimethyl-9H-pyrido[2,3-b]indol-9-yl)ethyl]-4-methoxybenzamide 2,2,2-Trifluoro-1-[1-(2-fluorobenzyl)-1H-pyrrolo[2,3-b]pyridin-3-yl]-1-ethanone 1-(1-Ethyl-1H-pyrrolo[2,3-b]pyridin-3-yl)-2,2,2-trifluoro-1-ethanone 2,2,2-Trifluoro-1-(1-[3-(trifluoromethyl)benzyl]-1H-pyrrolo[2,3-b]pyridin-3-yl)-1-ethanone 2-(2,4-Dimethyl-9H-pyrido[2,3-b]indol-9-yl)ethanamine dihydrochloride