Cesium fluoride → HCID 68863554, compound

Participants

Reaction Conditions

Reaction Steps

A solution of Example 110A (1.38 g, 3.0 mmol), dibutyl vinylboronate (0.83 g, 4.5 mmol), CsF (1.36 g, 9.0 mmol), and Pd(PPh3)4 (0.17 g, 0.15 mmol) in DME (12 mL) and methanol (6 mL) was purged with argon and stirred at 80° C. for 36 hours. The mixture was treated with brine (30 mL) and extracted with ethyl acetate. The ethyl acetate solution was dried (MgSO4), filtered and concentrated. The residue was purified by flash column chromatography on a silica gel with 30% ethyl acetate/hexanes to provide the desired product (0.57 g, 46.6%). 1H NMR (DMSO-d6) δ 2.12 (s, 3H), 5.26 (s, 2H), 5.34 (d, 1H), 5.65 (d, 1H), 6.86-6.91 (dd, 1H), 6.98 (d, 1H), 7.31-7.47 (m, 6H), 7.65 (m, 1H), 9.87 (d, 1H), 8.04 (dt, 1H), 8.74 (d, 1H), 10.04 (s, 1H); MS (ESI(+)) m/e 409 (M+H)+. Further elution of the column with 5% methanol in ethyl acetate with 0.1% acetic acid provided another white solid (0.125 g) which was identified as Example 172B.

Provenance & Evidence