Methanol → HCID 178448619, compound

Participants

Reaction Conditions

Reaction Steps

To a mixture of Example 11A (400 mg, 0.869 mmol), palladium acetate (19.5 mg, 0.087 mmol), dicyclohexyl(2′,6′-dimethoxybiphenyl-2-yl)phosphine (71.3 mg, 0.174 mmol) was added a solution of (3-ethoxy-3-oxopropyl)zinc(II) bromide (4.17 mL, 2.085 mmol) in tetrahydrofuran. This mixture was heated at 65° C. for 12 hours then cooled to room temperature and diluted with water and ethyl acetate. The organic layer was separated, dried (Na2SO4), filtered, and concentrated under reduced pressure. The residue was purified by column chromatography using an Analogix® Intelliflash280™ (SiO2, eluted with a gradient of 15-100% hexanes in solvent B, solvent B: 10:1:0.5 ethyl acetate:methanol:triethylamine) to afford the title compound (410 mg, 0.851 mmol, 98% yield). 1H NMR (300 MHz, CDCl3) δ ppm 0.96 (t, J=7.29 Hz, 3H) 1.19-1.23 (m, 3H) 1.37-1.41 (m, 2H) 1.44 (s, 9H) 1.64-1.74 (m, 2H) 2.73-2.78 (m, 2H) 3.40 (t, J=7.46 Hz, 2H) 3.80 (s, 3H) 4.10 (q, J=7.12 Hz, 2 H) 4.25-4.39 (m, 2H) 6.91-7.01 (m, 1H) 7.31-7.33 (m, 1H) 7.48 (dd, J=8.14, 1.36 Hz, 1 H) 8.17 (s, 1H); MS (DCI/NH3) m/z 482 (M+H)+.

Provenance & Evidence