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

pka

5.35±0.30(Predicted)

Appearance

Light yellow to green yellow Liquid

Safety Information

HS Code 

2933998090

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

Uses

N-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

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(27257-15-4)Related Product Information

• 2-(TERT-BUTYL)-1-(4-METHYLBENZYL)-1H-PYRROLO[2,3-B]PYRIDINE
• N-(3-CHLOROPHENYL)-N'-[2-(2,4-DIMETHYL-9H-PYRIDO[2,3-B]INDOL-9-YL)ETHYL]THIOUREA
• 2-(TERT-BUTYL)-1-METHYL-1H-PYRROLO[2,3-B]PYRIDINE
• N-[2-(2,4-DIMETHYL-9H-PYRIDO[2,3-B]INDOL-9-YL)ETHYL]-3,4,5-TRIMETHOXYBENZAMIDE
• 2-(TERT-BUTYL)-1-(2,4-DICHLOROBENZYL)-1H-PYRROLO[2,3-B]PYRIDINE
• 2-(TERT-BUTYL)-1-(3-METHYLBENZYL)-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-[3-(TRIFLUOROMETHYL)BENZYL]-1H-PYRROLO[2,3-B]PYRIDIN-3-YL)-1-ETHANONE
• 1-BENZYL-2-(TERT-BUTYL)-1H-PYRROLO[2,3-B]PYRIDINE
• 2-(2,4-DIMETHYL-9H-PYRIDO[2,3-B]INDOL-9-YL)ETHANAMINE DIHYDROCHLORIDE
• N-[2-(2,4-DIMETHYL-9H-PYRIDO[2,3-B]INDOL-9-YL)ETHYL]-3-FLUOROBENZAMIDE
• 1-[(2-CHLORO-1,3-THIAZOL-5-YL)METHYL]-1H-PYRROLO[2,3-B]PYRIDINE
• 2-CHLORO-N-[2-(2,4-DIMETHYL-9H-PYRIDO[2,3-B]INDOL-9-YL)ETHYL]BENZAMIDE
• N-[2-(2,4-DIMETHYL-9H-PYRIDO[2,3-B]INDOL-9-YL)ETHYL]-N'-(4-METHYLPHENYL)THIOUREA
• 1-(1-ETHYL-1H-PYRROLO[2,3-B]PYRIDIN-3-YL)-2,2,2-TRIFLUORO-1-ETHANONE
• 2-(TERT-BUTYL)-1-(3-FLUOROBENZYL)-1H-PYRROLO[2,3-B]PYRIDINE
• IMPLITAPIDE
• 2,2,2-TRIFLUORO-1-[1-(2-FLUOROBENZYL)-1H-PYRROLO[2,3-B]PYRIDIN-3-YL]-1-ETHANONE