Water → HCID 57985907, compound

Participants

Reaction Steps

To a RT solution of MeNH2.HCl (2.17 g, 31.9 mmol) in MeOH (40 mL) was added NaOH (319 mg, 7.98 mmol). The resulting mixture was stirred for 20 min. Then a solution of 3-(4-methoxy-pyrrolo[2,3-b]pyridin-1-yl)-3-phenyl-propionaldeyde (2.0 mmol) in MeOH (20 mL) was added, and the resulting mixture was stirred for 2 h. To this solution was added NaCNBH4 (125 mg, 2.0 mmol), and the mixture was stirred for 1 h, poured into water, and extracted with EtOAc. The organic layer was washed with water and brine, dried over MgSO4, filtered, concentrated, and purified via preparative TLC, affording [3-(4-Methoxy-pyrrolo[2,3-b]pyridin-1-yl)-3-phenyl-propyl]-methyl-amine (123 mg, 21% 3 steps yield). This compound was dissolved in EtOAc, and converted into the corresponding hydrochloride salt by the addition of 1 equivalent of HCl (1 M in Et2O) to give 107 mg of the corresponding HCl salt.

Provenance & Evidence