Acetic Acid → HCID 44548575, compound

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of 7-(5-{3-chloro-4-[(1-methylethyl)oxy]phenyl}-1,2,4-oxadiazol-3-yl)-1-methyl-1H-indole-3-carbaldehyde (D61) (200 mg), N-methylglycine (93 mg) and acetic acid (32 mg) in DCM (10 mL) was added NaBH(OAc)3 (223 mg). The reaction was stirred at 40° C. overnight. After cooled to room temperature, the reaction mixture was diluted with DCM (10 mL), washed with water (20 mL) and aqueous saturated sodium bicarbonate (20 mL). The organic phase was separated and dried over anhydrous sodium sulphate. After concentration, the residue was purified by Mass Directed Auto Prep to afford N-{[7-(5-{3-chloro-4-[(1-methylethyl)oxy]phenyl}-1,2,4-oxadiazol-3-yl)-1H-indol-3-yl]methyl}-N-methylglycine (E52) (210 mg, TFA salt). δH (DMSO-d6, 400 MHz): 1.36 (6H, d), 2.80 (3H, s), 4.01 (2H, s), 4.57 (2H, s), 4.90 (1H, m), 7.35 (1H, t), 7.46 (1H, d), 7.75 (1H, d), 8.01 (1H, d), 8.07 (1H, d), 8.21 (1H, dd), 8.39 (1H, d), 11.48 (1H, br s). MS (ES): C23H23ClN4O4 requires 454; found 366.1 (M—C3H6NO2+).

Provenance & Evidence