Hexane → HCID 67461249, compound

Participants

Reaction Steps

A solution of 40.0 mg (0.167 mmol, 1.0 eq) of alkyne 11b in 750 μL of dry Et3N was stirred in a 5 mL round bottom flask at room temperature under argon. To this solution was then added 23 μL (0.20 mmol, 1.2 eq) of iodobenzene. The resulting solution was sparged with argon for 5 minutes, at which time 6.0 mg (0.008 mmol, 0.05 eq) of PdCl2(PPh3)2 and 1.5 mg (0.008 mmol, 0.05 eq) of CuI were added and the reaction was stirred at room temperature until complete by TLC (1:1 hexane:EtOAc, Rf=0.42). Upon completion (˜5 hours) the solution was diluted with Et2O and washed sequentially with 1.0 M HCl and H2O. The organic fraction was then dried over MgSO4, concentrated and purified via silica gel chromatography (hexane/EtOAc) to give 44 mg (83%) of 11d as a pale brown oil, Rf 0.42 (1:1 hexane:EtOAc). 1H-NMR (500 MHz, CDCl3): 7.89 (1H, s), 7.82 (1H, d, J=7.3 Hz), 7.57 (1H, dt, J=7.8 Hz, 1.9 Hz), 7.42 (1H, m), 7.38 (1H, m), 7.34 (2H, m), 7.28 (3H, m), 4.34 (1H, q, J=7.1 Hz), 2.37 (3H, s), 1.62 (3H, d, 7.1 Hz). 13C-NMR (500 MHz, CDCl3): 185.67, 152.11, 146.95, 145.47, 142.66, 136.49, 131.69, 131.68, 128.64, 128.37, 128.19, 128.07, 126.62, 123.55, 92.70, 82.47, 29.37, 24.61, 14.18. IR (cm−1): 1653 (vs), 1579 (s), 1487 (m), 1442 (w), 1384 (m), 1355 (m), 900 (m), 757 (s). HRMS (EI) calcd. for C21H17NO2: 315.1259. found: 315.1244.

Provenance & Evidence