Methylamine → HCID 67216563, compound

Participants

Reaction Steps

Methylamine gas was bubbled into a solution of 2-(4-chloro-1-tosyl-1H-pyrrolo[2,3-b]pyridin-5-yl)acetaldehyde (1.45 g, 4.16 mmol) in DCE (50 mL) for about 10 min. NaBH(OAc)3 (1.69 g, 7.97 mmol) was added and the mixture was stirred at rt. After about 45 min, the mixture was concentrated under reduced pressure then dissolved in MeOH (25 mL) and treated with NaBH4 (0.236 g, 6.24 mmol). After about 10 min, the mixture was concentrated under reduced pressure then partitioned between DCM (50 mL), saturated aqueous NaHCO3 (20 mL) and water (30 mL). The layers were separated then the aqueous layer was extracted with DCM (20 mL). The organic layers were combined, dried over anhydrous MgSO4, filtered and concentrated in vacuo. The material was purified by preparative reverse phase HPLC (Table 2, Method i). The desired fractions were collected then most of the MeCN was removed under reduced pressure. The solution was basified with saturated aqueous NaHCO3 and the solids were collected by filtration to give 2-(4-chloro-1-tosyl-1H-pyrrolo[2,3-b]pyridin-5-yl)-N-methylethanamine (0.67 g, 44%): LC/MS (Table 2, Method a) Rt=1.88 min; MS m/z 364 (M+H)+.

Provenance & Evidence