Phenylacetylene → HCID 67361701, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 28 (200 mg, 0.54 mmol), phenylacetylene (83 mg, 0.81 mmol), [Cu(Phen)(PPh3)2]NO3 (45 mg, 54.0 μmol), K3PO4 (230 mg, 1.08 mmol) and anhydrous DMF (5 mL) was flushed with argon and stirred for 2 days at 115° C. After removal of the solvent, the residue was diluted with H2O (25 mL) and extracted with CH2Cl2 (5×20 mL). The CH2Cl2 extracts were dried (Na2SO4), filtered and evaporated. The residue was purified by chromatography using CH2Cl2/EtOAc (4/1, v/v) as eluent to afford compound 29 (75 mg, yield: 56%); mp 222° C.; IR (KBr) 3026, 3057, 2944, 2824, 1641, 1604, 1535 cm−1; 1H NMR (400 MHz, DMSO-d6) δ 2.3 (s, 3H), 6.96 (d, 1H, J=7.2 Hz), 7.15 (s, 1H), 7.29 (t, 1H, J=7.4 Hz), 7.46 (t, 2H, J=7.8 Hz), 7.50 (s, 1H), 7.85 (d, 2H, J=8.4 Hz), 8.06 (d, 1H, J=7.2 Hz), 11.98 (s, 1H); 13C NMR (100 MHz, DMSO-d6) δ 14.2, 98.1, 100.6, 109.3, 114.2, 120.9, 124.5, 127.1, 128.9, 131.4, 131.9, 135.7, 139.1, 140.7. Anal. Calcd for C16H13N3: C, 77.71; H, 5.30; N, 16.99. Found: C, 77.69; H, 5.41; N, 16.94.

Provenance & Evidence