Dimethylformamide → HCID 69219560, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of Example 515B (210 mg, 0.5 mmol), tributyl(vinyl)tin (175 μL, 0.6 mmol), Pd(PPh3)2Cl2 (35 mg, 0.05 mmol), LiCl (169 mg, 4.0 mmol) and DMF was flushed with nitrogen, heated at 50° C. overnight, cooled to room temperature, diluted with a saturated potassium fluoride solution, stirred 15 minutes, diluted with ethyl acetate, washed with water and brine, dried (MgSO4), filtered, and concentrated under vacuum. The residue was purified by column chromatography on silica gel with a solvent gradient of 4:1 to 1:1 hexane/ethyl acetate to give 77 mg (52%) of the desired product. MS (ESI) m/e 301 (M+H)+; 1H NMR (300 MHz, DMSO-d6) □ 9.72 (s, 1H), 8.14 (s, 1H), 7.68 (d, J=8.5 Hz, 1H), 7.11 (s, 1H), 7.05 (d, J=2.0 Hz, 1H), 6.94 (dd, J=2.0, 8.5 Hz, 1H), 6.80 (dd, J=11.2, 18.0 Hz, 1H), 6.63 (s, 1H), 5.56 (dd, J=1.5, 17.8 Hz, 1H), 5.14 (dd, J=1.7, 11.2 Hz, 1H), 3.75 (s, 3H).

Provenance & Evidence