Dimethylformamide → HCID 66865502, compound

Participants

Reaction Steps

[4-(3-Cyano-1-ethyl-6-methoxy-1H-indol-2-yl)-phenoxy]-acetic acid (40 mg, 0.12 mmol) was suspended in CH2Cl2 (1.65 mmol) and DMF (2 μL). Oxalyl chloride (17 μL, 0.19 mmol) was added. This was stirred at room temperature for 30 minutes. The resulting solution was then pipetted into a stirring solution of S-3-hydroxypyrrolidine (150 μL) and CH2Cl2 (3.0 mL). The mixture was washed with aqueous HCl. The organic layer was dried and concentrated. Purification by silica gel chromatography (3/2 CH2Cl2/acetone) yielded 1-ethyl-2-{4-[2-(3-hydroxy-pyrrolidin-1-yl)-2-oxo-ethoxy]-phenyl}-6-methoxy-1H-indole-3-carbonitrile (40 mg, 79%), compound 285 as a white solid.

Provenance & Evidence