Hydrochloric Acid → HCID 70652010, compound

Participants

Reaction Conditions

Reaction Steps

A solution of ethyl 5-bromo-8-carbamoyl-9H-pyrido[3,4-b]indole-3-carboxylate (0.4 g, 1.104 mmol) in THF (31.6 mL) was cooled in a salt-ice bath slowly treated with methylithium (1.6 M in ether, 3.80 mL, 6.07 mmol). The solution was stirred at −5° C. for 1.5 h, then was treated with ice and 1 M aqueous HCl (7 mL). The mixture was made basic with NaHCO3 (aq) and extracted with chloroform-isopropanol (3:1). The organic phase was washed with brine, dried and concentrated. The residue was subjected to column chromatography on silica gel (40 g), eluting with Methanol-CH2Cl2 (gradient from 2:98 to 10:90) to provide the desired product as a yellow solid (128 mg, 33% yield). LCMS (M+H)+ m/z 347.9, 349.9.

Provenance & Evidence