Triethylamine → (R)-3-((1-(1H-indole-2-carbonyl)pyrrolidin-2-yl)methoxy)picolinamide

Participants

Reaction Steps

A mixture of (R)-3-(pyrrolidin-2-ylmethoxy)picolinamide dihydrochloride (25 mg, 0.085 mmol, EXAMPLE 1 Step 3), indole-2-carboxylic acid (15 mg, 0.093 mmol), triethylamine (0.060 mL, 0.43 mmol), and N,N,N′,N′-tetramethyl-O-(1H-benzotriazol-1-yl)uronium hexafluorophosphate (HBTU) (48 mg, 0.13 mmol) in acetonitrile (1 mL) was stirred at room temperature for 4 h. The mixture was poured into water, and the aqueous layer was extracted with dichloromethane twice. The combined organic layers were dried over magnesium sulfate and concentrated in vacuo. The residual solid was washed with methanol to give 22 mg (71%) of the title compound as a white solid.

Provenance & Evidence