Water → Trifluoroacetic acid

Participants

Reaction Conditions

Reaction Steps

A heavy-walled glass vial was charged with (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 (13 mg), 1-(5-bromopyrimidin-2-yl)azetidin-3-ol trifluoroacetic acid salt (18 mg), Cs2CO3 (18 mg), water (0.1 mL), and 1,4-dioxane (1 mL). The mixture was sparged with N2 for 10 min before PdCl2[1,1′-bis(diphenylphosphino)ferrocene] (2 mg) was added. The mixture was sparged with N2 for 10 min and then heated in a microwave oven at 110° C. for 30 min. After cooling to room temperature, the reaction mixture was purified by preparative HPLC to afford the title compound as its trifluoroacetic acid salt as an oil. Yield: 12.1 mg (89% of theory); LC (method 5): tR=1.3 min; Mass spectrum (ESI+): m/z=503 [M+H]+; 1H NMR (CD3OD) δ 0.95 (s, 3H), 1.26 (s, 3H), 1.56 (d, 3H), 2.16 (s, 2H), 2.23 (m, 1H), 2.47 (m, 2H), 3.05 (m, 1H), 4.07 (m, 2H), 4.49 (m, 2H), 4.73 (m, 1H), 5.57 (q, 1H), 7.09 (d, 2H), 7.25-7.40 (7H), 8.63 (s, 2H).

Provenance & Evidence