1-Bromopropane → HCID 25142826, compound

Participants

Reaction Steps

(1R,2R)-2-(6-Hydroxy-1,3,4,5-tetrahydro-pyrido[4,3-b]indole-2-carbonyl)-cyclohexanecarboxylic acid (1-cyano-cyclopropyl)-amide (102 mg, 0.25 mmol), 1-bromopropane (28.0 uL, 0.30 mmol) and potassium carbonate (35.0 mg, 0.25 mmol) in acetone (5 mL) were heated to reflux for 3 h. Added further 1-bromopropane (58.0 uL, 0.60 mmol) and potassium carbonate (70.0 mg, 0.50 mmol) and heated overnight. The reaction darkened significantly and LCMS indicated 60% required product and 40% SM. The reaction was filtered and the liquors evaporated to dryness before redissolving in acetonitrile and purifying by preparative HPLC (0.5% HCOOH, CH3CN/H2O gradient) to give a brown glass (21.3 mg, 18%)

Provenance & Evidence