2-Dicyclohexylphosphino-2',6'-dimethoxybiphenyl → HCID 178480266, compound

Participants

Reaction Conditions

Reaction Steps

A solution of (2-tert-butoxy-2-oxoethyl)zinc(II) bromide (2.13 mL, 1.07 mmol) in ether (3 mL) was added to a mixture of Example 88 (260 mg, 0.532 mmol), palladium acetate (12.0 mg, 0.053 mmol), and dicyclohexyl(2′,6′-dimethoxybiphenyl-2-yl)phosphine (82 mg, 0.20 mmol). The mixture was stirred at 50° C. overnight then quenched with saturated aqueous ammonium chloride and extracted with ethyl acetate (3×10 mL). The organic extracts were combined, washed with water, dried (MgSO4), filtered, and concentrated. The residue was purified by column chromatography using an Analogix® Intelliflash280™ (SiO2, 15-100% solvent A in hexanes, solvent A=10:1:0.5 ethyl acetate:methanol:triethyl amine) to afford the title compound (0.19 g, 0.363 mmol, 68.2% yield). 1H NMR (300 MHz, CDCl3) δ ppm 1.41 (s, 9H) 1.42 (s, 9H) 1.72-1.88 (m, 3H) 2.00-2.10 (m, 1H) 3.62 (q, J=7.27 Hz, 1H) 3.68-3.82 (m, 2H) 3.87 (s, 3H) 4.19 (d, J=7.93 Hz, 2H) 4.23-4.32 (m, 1 H) 4.53-4.61 (m, 1H) 7.01 (s, 1H) 7.30 (d, J=8.33 Hz, 1H) 7.51 (dd, J=8.13, 1.39 Hz, 1H) 8.38 (s, 1H); MS (DCI/NH3) m/z 524 (M+H)+.

Provenance & Evidence