Triethylamine → HCID 86606905, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of Example 240B (95 mg, 0.2 mmol), ethynyltrimethylsilane (59 mg, 0.6 mmol), PdCl2 (Ph3P)2 (7 mg, 0.01 mmol), CuI (4 mg, 0.02 mmol) and triethylamine (40 mg, 0.4 mmol) in N,N-dimethylformamide (2 ml) was sealed in a tube and heated at 110° C. for 6 hours, checked with LC/MS until starting material disappeared. The mixture was filtered and the filtrate was partitioned between ethyl acetate and water (30 ml, 1:1). The organic layer was washed with brine, dried over MgSO4, filtered, and evaporated in vacuo. The crude product was purified on silica gel cartridge by Anal.ogix eluting with 100% ethyl acetate to give the titled compound (32 mg, 30%). 1H NMR (300 MHz, DMSO-d6) δ ppm 9.03 (t, J=6.44 Hz, 1H), 7.87 (d, J=8.48 Hz, 2H), 7.55 (d, J=8.14 Hz, 2H), 7.06 (s, 1H), 6.75 (s, 1H), 6.05 (s, 2H) 4.57 (d, J=6.44 Hz, 2H), 4.36 (q, J=6.95 Hz, 2H), 3.17 (s, 3H), 1.29 (t, J=6.95 Hz, 3H), 0.21 (s, 9H), 0.11 (s, 9H); MS (APCI) m/z 544 [M+H]+, 542 [M−H]−.

Provenance & Evidence