Cesium fluoride → HCID 20781256, compound

Participants

Reaction Conditions

Reaction Steps

Nitrogen was bubbled through a solution containing the product of Example 47 (1.0 g, 1.93 mmol), tri-t-butylphosphine (0.1 M in dioxane, 190 μl, 0.19 mmol), cesium fluoride (0.65 g, 4.28 mmol) and Pd2(dba)3 (0.10 g, 0.11 mmol) in dioxane (8 ml) in a sealed tube for 5 minutes. Tributyl(vinyl)tin (0.65 g, 2.05 mmol) was added and the mixture heated at 100° C. for 2 hours. This sequence was repeated on the same scale a further four times. All five reaction mixtures were combined and diluted with diethyl ether (50 ml) and filtered through a silica gel pad, evaporated in vacuo to give crude product which was chromatographed on silica eluting with 5-20% ethyl acetate/isohexane, then azeotroped with dichloromethane to give the desired product (2.67 g, 55%). 1H NMR (CDCl3, 360 MHz): 1.59-1.70 (2H, m), 2.02-2.06 (2H, m), 2.44 (2H, t, J=12.7 Hz), 2.61-2.65 (2H, m), 3.78 (1H, m), 5.47 (1H, d, J=10.9 Hz), 5.82 (1H, bd, J=7.8 Hz), 5.88 (1H, d, J=17.5 Hz), 6.68-6.87 (1H, m), 7.01-7.08 (2H, m), 7.32 (2H, d, J=8.3), 7.40 (2H, d, J=8.1), 10.10 (1H, s)

Provenance & Evidence