Triethylamine → HCID 57965691, compound

Participants

Reaction Steps

A mixture of (2-acryloylamino-phenyl)-carbamic acid tert-butyl ester (20.0 g, 76.3 mmol), 4-bromobenzaldehyde (14.4 g, 77.8 mmol), Pd2(dba)3 (0.56 g, 0.61 mmol), tri-o-tolyphosphine (0.370 g, 1.22 mmol) and triethylamine (42.1 mL, 0.300 mol) in DMF (300 mL) was stirred at 100 degrees Celsius under N2 for 5 hours. The reaction mixture was allowed to cool down to room temperature and poured into a saturated aqueous solution of NH4Cl. The precipitate was filtered off and washed with water, dried in vacuo at 40° C. overnight. The crude product was purified by flash column chromatography to obtain a yellow solid (15.5 g, 56%). MS: calc'd 367 (MH+), exp 367 (MH+). 1H NMR (d6-DMSO, 400 MHz) δ 10.0 (s, 1H), 9.79 (s, 1H), 8.53 (s, 1H), 7.98 (d, 2H, J=8.0 Hz), 7.87 (d, 2H, J=8.0 Hz), 7.68 (d, 1H, J=16 Hz), 7.60 (m, 2H), 7.14 (m, 2H), 7.10 (d, 1H, J =16 Hz), 1.46 (s, 9H).

Provenance & Evidence