1H-PYRROLO[2,3-B]PYRIDINE, 2-METHYL- Chemical Properties

Melting point:

136-142℃

Density 

1.17

storage temp. 

Sealed in dry,Room Temperature

solubility 

Chloroform (Slightly), Methanol (Slightly)

form 

Solid

pka

14.45±0.40(Predicted)

color 

Brown

CAS DataBase Reference

23612-48-8

Safety Information

HS Code 

29339900

1H-PYRROLO[2,3-B]PYRIDINE, 2-METHYL- Usage And Synthesis

Chemical Properties

White powder

Uses

2-Methyl-7-Azaindole can be used to fingerprint volatile profile of traditional tobacco and e-cigarettes.

Synthesis

Under nitrogen protection, tert-butyl 3-methylpyridin-2-ylcarbamate (5.07 g, 23.6 mmol) was dissolved in 100 mL of tetrahydrofuran and the mixture was cooled to -10 °C. Under stirring, n-butyllithium (2.5 M hexane solution, 28 mL, 70 mmol) was slowly added over 15 min and the reaction solution turned dark red, and stirring was continued at -10 °C for 1 hr. Subsequently, N-methoxy-N-methylacetamide (3.80 g, 35.7 mmol) was added and the mixture was warmed to room temperature and stirred for 1 hour. Upon completion of the reaction, the mixture was cooled again to -10 °C, the reaction was quenched with 13 mL of concentrated hydrochloric acid, and then stirred at 50 °C for 90 min. After the two-phase mixture was cooled, the organic phase was separated and extracted twice with 2N hydrochloric acid. The aqueous phases were combined, alkalized to the proper pH with 32% sodium hydroxide solution and subsequently extracted three times with ethyl acetate. The organic phases were combined, washed with saturated saline, dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure. The crude product was purified by Isolera purification system (ethyl acetate-hexane gradient, 0:100 ascending to 50:50) to afford 2-methyl-7-azaindole (2.5 g, 18.9 mmol, 80% yield) as a light yellow solid with 100% purity.1H NMR (400 MHz, CDCl3) δ ppm 2.55 (s, 3H, Me) 6.17 (s, 1H, H-3), 7.03 (dd, J = 4.9, 7.6 Hz, 1H, H-5), 7.82 (d, J = 7.4 Hz, 1H, H-4), 8.21 (d, J = 4.7 Hz, 1H, H-6), 11.96 (br.s, 1H, NH).UPLC/MS (3 min) retention time 0.68 min. LRMS: m/z 133 (M + 1).

References

[1] European Journal of Medicinal Chemistry, 2016, vol. 113, p. 102 - 133

1H-PYRROLO[2,3-B]PYRIDINE, 2-METHYL-(23612-48-8)Related Product Information

• BOC,BZL-L-ALA-OH
• Pyrido[4,3-d]pyrimidin-4(1H)-one (9CI)
• 1H-Pyrrole-2-acetic acid, 3-(methoxycarbonyl)-1-methyl-, methyl ester
• 3-Trifluoromethyl-1H-pyrrolo[2,3-b]pyridine
• 6-Bromoisatin
• 7-bromo-4-(trifluoromethyl)-1H-indole
• 2-iodo-1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridine
• 3-BROMO-1H-PYRROLE-2-CARBOXYLIC ACID METHYL ESTER
• SW-80
• methyl exo-3-azabicyclo[3.1.0]hexane-6-carboxylate hydrochloride
• LY-2484595
• (1s,3r,4r)-3-[(tert-butoxycarbonyl)amino]-4-[(methylsulfonyl)oxy]cyclohexanecarboxylic acid ethyl ester
• 1H-PYRROLO[2,3-B]PYRIDINE-2-CARBOXYLIC ACID
• 1H-Pyrrolo[2,3-b]pyridine, 2,3-dimethyl-
• 2-(TERT-BUTYL)-1H-PYRROLO[2,3-B]PYRIDINE
• 2,4-DIMETHYL-A-CARBOLINE
• 2-phenyl-1H-pyrrolo[2,3-b]pyridine
• [1-(PHENYLSULFONYL)-1H-PYRROLO[2,3-B]PYRIDIN-2-YL](2-THIENYL)METHANOL