Hydrochloric Acid → 1-benzyl-4-(4-chlorophenyl)-5-(hydroxymethyl)-6-methyl-1H-pyrrolo[2,3-c]pyridin-7(6H)-one

Participants

Reaction Conditions

Reaction Steps

A solution of methyl 1-benzyl-4-(4-chlorophenyl)-6-methyl-7-oxo-6,7-dihydro-1H-pyrrolo[2,3-c]pyridine-5-carboxylate (6.4 g, 15.7 mmol) in Toluene (80 mL) was treated with LiBH4 (3.43 g, 157 mmol) and then heated at 90° C. overnight. Additional LiBH4 (3.43 g, 157 mmol) was added and the mixture was allowed to stir for an additional 5 hours at 90° C. The mixture was cooled to 0° C., treated with HCl (1M) until pH<2 and then extracted with ethyl acetate. The combined extracts were washed with brine, dried over Na2SO4, filtered and concentrated. The residue was purified on silica gel (0-100% ethyl acetate/hexanes) to afford 1-benzyl-4-(4-chlorophenyl)-5-(hydroxymethyl)-6-methyl-1H-pyrrolo[2,3-c]pyridin-7(6H)-one (4.0 g, 10.6 mmol, 67% yield) as a white solid. 1H NMR (400 MHz, DMSO-d6) ppm 7.53-7.57 (m, 2H) 7.43-7.47 (m, 4H) 7.28-7.35 (m, 4H) 5.92-5.96 (m, 1H) 5.80 (s, 2H) 5.31 (s, 1H) 4.29-4.37 (m, 2H) 3.70 (s, 3H); LCMS (m/z) ES+=379 (M+1).

Provenance & Evidence