Propyne → HCID 57800251, compound

Participants

Reaction Conditions

Reaction Steps

A triethylamine (300 mL) solution of N-[4-chloro-2-iodo-3-(trifluoromethyl)phenyl]-2,2-dimethylpropanamide (Example 60A) (40 g, 98.6 mmol) was treated with 1-propyne (39.5 g, 988 mmol) followed by copper iodide (0.94 g, 4.9 mmol) and PdCl2(PPh3)2 (6.9 g, 9.8 mmol) in a Parr Bomb at −78° C. The reaction vessel was purged with N2, sealed and heated gradually to 50° C. overnight, then cooled to −78° C. The cooled mixture was diluted with Et2O and filtered through celite. The Et2O solution was washed with water once, brine once, and dried (MgSO4). Filtration and concentration in vacuo followed by radial chromatography (SiO2, 0-10% EtOAc-hexanes gradient) afforded the title compound as a yellow solid (20.5 g, 65%): 1H NMR (400 MHz, CDCl3) δ 8.70 (s, 1H), 8.60 (d, J=9.0 Hz, 1H), 7.38 (d, J=9.0 Hz, 1H), 2.22 (s, 3H), 1.33 (s, 9H); MS (ES) m/z 318 (M+1) and 320 (M+1, isotope).

Provenance & Evidence