Tributylphosphine → HCID 59375030, compound

Participants

Reaction Steps

Step 2 A solution of N-(3-bromo-2-methylphenyl)-5-cyano-2-(hydroxymethyl)benzamide (170 mg, 0.492 mmol) in THF (20 mL) was treated with di-tert-butyl azodicarboxylate (113 mg, 0.492 mmol) and tributylphosphine (0.119 mL, 0.492 mmol) and stirred at rt. After 2 h the mixture was concentrated and the residue was column chromatography (eluting with a gradient from 90:10 to 50:50 hexane-EtOAc) to provide 2-(3-bromo-2-methylphenyl)-3-oxoisoindoline-5-carbonitrile (100 mg, 62%) as a white solid. 1H NMR (400 MHz, chloroform-d) δ 8.07 (1 H, d, J=8.1 Hz), 7.82-7.89 (2 H, m), 7.64 (1 H, dd, J=7.8, 1.4 Hz), 7.13-7.25 (2 H, m), 4.78 (2 H, s), 2.30 (3 H, s). Mass spectrum m/z 327, 329 (M+H)+.

Provenance & Evidence