Sodium Carbonate → HCID 54770619, compound

Participants

Reaction Conditions

Reaction Steps

2 M aqueous Na2CO3 solution (0.21 mL) was added to a solution of (S)-6-(2-hydroxy-2-methylpropyl)-6-phenyl-3-{(S)-1-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]-ethyl}-1,3-oxazinan-2-one (100 mg) and 3-(4-bromo-phenyl)-oxetan-3-ol (53 mg) in N,N-dimethylformamide (2 mL). The resulting mixture was sparged with argon for 10 min prior to the addition of [1,1′-bis(diphenylphosphino)ferrocene]-dichloropalladium(II) dichloromethane complex (17 mg). The mixture was heated to 100° C. and stirred at this temperature for 4 h. After cooling to ambient temperature, water was added and the resulting mixture was extracted with ethyl acetate. The combined organic extracts were washed with brine, dried (MgSO4), and concentrated. The residue was purified by HPLC on reversed phase (acetonitrile/water) to afford the title compound as a foam-like solid. Yield: 34 mg (32% of theory); Mass spectrum (ESI+): m/z=502 [M+H]+; 1H NMR (400 MHz, DMSO-d6) δ 0.82 (s, 3H), 1.19 (s, 3H), 1.47 (d, J=6.9 Hz, 3H), 2.02 (s, 2H), 2.15 (mc, 1H), 2.38-ca. 2.50 (m, 2H) superimposed by D3CSOCHD2 signal, 3.01 (mc, 1H), 4.23 (s, 1H), 4.70 (d, J=6.3 Hz, 2H), 4.79 (d, J=6.3 Hz, 2H), 5.44 (incompletely resolved q, 1H), 6.35 (s, 1H), 6.94 (d, J=7.9 Hz, 2H), 7.26-7.43 (m, 7H), 7.59 (d, J=8.2 Hz, 2H), 7.66 (d, J=8.2 Hz, 2H).

Provenance & Evidence