Triethylamine → HCID 59316974, compound

Participants

Reaction Conditions

Reaction Steps

A solution of 3-(3-bromophenyl)-1,1-dipropylurea (24) (0.507 g, 1.70 mmol), tert-butyl prop-2-ynylcarbamate (15) (0.323 g, 2.12 mmol), tri-o-tolylphosphine (0.0342 g, 0.112 mmol) and Et3N (3.0 mL) in DMF was degassed by bubbling argon for 10 min, and applying vacuum/argon 3×. PdCl2(Ph3P)2 (0.0434 g, 0.062 mmol) followed by CuI (0.0263 g, 0.138 mmol) were added and the mixture was degassed by applying vacuum/argon 3×. The reaction mixture was stirred under argon at 70° C. for 22 hrs. The reaction mixture was concentrated under reduced pressure. Purification by flash chromatography (10% to 50% EtOAc—hexanes gradient) gave tert-butyl 3-(3-(3,3-dipropylureido)phenyl)prop-2-ynylcarbamate (25) as a pale yellow solid. Yield (0.174 g, 28%); 1H NMR (400 MHz, DMSO-d6) δ 8.15 (br.s, 1H), 7.56 (t, J=1.8 Hz, 1H), 7.42-7.46 (m, 1H), 7.31 (br.t, 1H), 7.17 (t, J=7.8 Hz, 1H), 6.89-6.93 (m, 1H), 3.93 (d, J=5.7 Hz, 2H), 3.21 (t, J=7.6 Hz, 4H), 1.47 (sextet, J=7.4 Hz, 4H), 1.32-1.38 (m, 9H), 0.82 (t, J=7.4 Hz, 6H).

Provenance & Evidence