Tetrahydrofuran → HCID 66816934, compound

Participants

Reaction Steps

A mixture of oxazole-2-carboxylic acid (147 mg) and DMF (2 drops) in DCM (1 mL) was treated with oxalyl chloride (127 μL). Gas evolution ceased after 2 h. CHCl3 (2 mL) was added, the volatiles removed in a vacuum oven (40° C., 200 mbar), and the residual oil dissolved in THF (2 mL) to form “solution A”. A mixture of 1-{4-chloro-2-[6-(2,5-dimethyl-pyrrol-1-yl)-pyridin-2-ylamino]-phenyl}-3-phenyl-propan-1-one (430 mg) in THF (2 mL) was treated with DMF (2 drops) and NaHMDS solution (2.5 mL, 1 M in THF) was added dropwise. Solution A (2 mL) was added dropwise, and the mixture stirred at RT for 12 h. The product was worked up in EtOAc/H2O and chromatographed (DCM/MeOH 100:0 to 70:30) to provide 3-benzyl-7-chloro-1-[6-(2,5-dimethyl-pyrrol-1-yl)-pyridin-2-yl]-2-oxazol-2-yl-1H-quinolin-4-one.

Provenance & Evidence