Ethyl oxoacetate → HCID 178472699, compound

Participants

Reaction Conditions

Reaction Steps

To a suspension of (±)-tert-butyl 4-(1-amino-1-(5-cyano-1H-benzo[d]imidazol-2-yl)-2,2,2-trifluoroethyl)-5-methoxy-7-methyl-1H-indole-1-carboxylate (Example 139-A) (117 mg, 0.234 mmol) in DCE (2.34 mL) was added ethyl glyoxylate (50% in toluene) (93 μL, 0.468 mmol) and this was stirred at 60° C. After 5 minutes this was cooled to room temperature, then sodium triacetoxyborohydride (298 mg, 1.405 mmol) was added and this was stirred again at 60° C. After stirring overnight the reaction was quenched with sat. aq. sodium bicarbonate, extracted with EtOAc, dried with MgSO4, filtered and concentrated. The resulting residue was purified by flash chromatography (0-50% EtOAc in heptanes) to provide the title compound. MS (ESI+) m/z 586.3 (M+H).

Provenance & Evidence