HCID 86633500, compound → HCID 86633502, compound

Participants

Reaction Steps

To a cooled (0° C.) suspension of methyltriphenyl phosphonium bromide (5.33 g, 14.9 mmol) in THF (100 mL) was added dropwise n-BuLi (5.5 mL, 2.5 M in hexanes, 13.8 mmol). After aging for 40 min, the reaction mixture was allowed to warm up to ambient temperature for 25 min, at which point 7.4 mL of the supernatant was taken and added to the title compound from Example 302 Step D (270 mg, 0.442 mmol). After 30 min, the mixture was quenched by addition of water and the aqueous phase was extracted with hexane-EtOAc. The organic phase was separated and concentrated in vacuo. Purification by silica gel flash chromatography (5% to 15% EtOAc in hexanes) provided the title compound: LCMS m/z 590.5 [M−F]+; 1H NMR (500 MHz, CD2Cl2) δ 8.13 (s, 1H), 7.86 (m, 2H), 7.77 (m, 2H), 7.60 (d, J=8.0 Hz, 1H), 7.55-7.48 (m, 2H), 7.45-7.40 (m, 3H), 7.08 (m, 1H), 5.68 (d, J=17.2 Hz, 1H), 5.32 (d, J=11.0 Hz, 1H), 4.38 (q, J=7.2 Hz, 2H), 1.40 (t, J=7.2 Hz, 3H).

Provenance & Evidence