Diisopropylethylamine → HCID 67125657, compound

Participants

Reaction Conditions

Reaction Steps

A solution of 3-(2-cyanopropan-2-yl)benzoic acid 3 (2.64 mmol, 500 mg), TBTU (2.77 mmol, 891 mg) and DIPEA (5.29 mmol, 0.873 mL) in DMF (4 mL) was stirred at 50° C. for 15 min. 3-iodo-4-methylaniline (2.77 mmol, 647 mg) was added and stirred overnight at 50° C. Quenched in citric acid solution and extracted with ethyl acetate. Organic layer was washed with brine, dried and evaporated. Purification with chromatography (30% ethyl acetate in heptane) gave 3-(2-cyanopropan-2-yl)-N-(3-iodo-4-methylphenyl)benzamide 111 (861 mg, 81%). NMR (400 MHz, CDCl3) 1.78 (s, 6H), 2.42 (s, 3H), 7.23 (d, J=8.2 Hz, 1H), 7.52 (dd, J=8.2 Hz and 7.4 Hz, 1H), 7.58 (dd, J=8.2 Hz and 2.3 Hz, 1H), 7.71 (dq, J=7.8 Hz and 1.2 Hz), 7.76 (m, 1H), 7.78 (m, 1H), 7.96 (t, J=1.6 Hz, 1H), 8.11 (d, J=2.3 Hz, 1H).

Provenance & Evidence