Formaldehyde → HCID 57732871, compound

Participants

Reaction Steps

To a solution of 3-[1-(ethylsulfonyl)-4-piperidinyl]-5-(5-formyl-3-thienyl)-1H-indole-7-carboxamide (45 mg, 0.1 mmol) in dimethyl sulfoxide (1 mL) was added 2-butanamine (1 mmol), 1 to 2 drops of acetic acid and sodium triacetoxyborohydride (211 mg, 1 mmol). The resulting mixture was capped and stirred for 18 h followed by an addition of sodium cyanoborohydride (62 mg, 1 mmol) in methanol (0.5 mL). This was stirred for 3 h followed by an addition of formaldehyde, 37% in water, (1.5 mL). This was purified through SCX (2 g) cartridge eluting with methanol followed by NH3 in methanol. Further purification was performed by Gilson Preparatory HPLC. XBridge C18 Column (P/N 186002978) using a gradient of 10% acetonitrile to 70% acetronile in water with 0.1% NH4OH to give 14.4 mg of the title compound (27.9%).

Provenance & Evidence