تفاعل #749005

معادلة التفاعل

N-(3-bromo-2-methylphenyl)-5-cyano-2-(hydroxymethyl)benzamide

di-tert-butyl azodicarboxylate

tributylphosphine

→

2-(3-bromo-2-methylphenyl)-3-oxoisoindoline-5-carbonitrile

المردود 62.1%

المذيبات

THF

ظروف التفاعل

المعالجة

1. 1
   تركيزAfter 2 h the mixture was concentrated
2. 2
   غسيلeluting with a gradient from 90:10 to 50:50 hexane-EtOAc)

الإجراء التجريبي

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 (1H, d, J=8.1 Hz), 7.82-7.89 (2H, m), 7.64 (1H, dd, J=7.8, 1.4 Hz), 7.13-7.25 (2H, m), 4.78 (2H, s), 2.30 (3H, s). Mass spectrum m/z 327, 329 (M+H)+.

المصدر