Sodium borohydride → HCID 178489063, compound

Participants

Reaction Steps

To a solution of (±)-methyl 3-(5-cyano-1H-benzo[d]imidazol-2-yl)-3-(5-methoxy-7-methyl-1H-indol-4-yl)propanoate (Example 145-C) (50 mg, 0.129 mmol) in MeOH (1.3 mL) was added NaBH4 (121 mg, 3.25 mmol) at 0° C. The reaction mixture was allowed to reach rt and stirred for 48 hrs. The reaction mixture was quenched with water at 0° C. and extracted with EtOAc (2×). The combined organic layers were passed through a phase separator and concentrated and absorbed onto silica to purify via FCC with DCM/MeOH (100/0 to 95/5) to obtain the title compound. 1H NMR (400 MHz, DMSO-d6) δ ppm 12.04-12.30 (m, 1H) 10.89 (br. s., 1H) 8.10 (s, 1H) 7.68-7.77 (m, 1H) 7.38-7.51 (m, 1H) 6.99-7.21 (m, 1H) 6.78 (s, 1H) 6.10 (br. s., 1H) 4.99 (t, J=7.33 Hz, 1H) 4.36-4.57 (m, 1H) 3.74 (s, 3H) 3.42 (td, J=11.56, 5.68 Hz, 2H) 2.77 (dd, J=13.39, 6.82 Hz, 1H) 2.44 (s, 3H) 2.11-2.23 (m, 1H). HRMS calcd. for C21H20N4O2 (M+H)+ 361.1651. found 361.1659.

Provenance & Evidence