Water → HCID 44512092, compound

Participants

Reaction Conditions

Reaction Steps

A microwave vial, equipped with a flea stir bar, was charged with (S)-3-((S)-1-(4-bromophenyl)ethyl)-6-(2-hydroxy-2-methylpropyl)-6-phenyl-1,3-oxazinan-2-one (22 mg, 0.051 mmol), 2-tert-butoxy-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrazine (21 mg, 0.076 mmol), Cs2CO3 (33 mg, 0.10 mmol), water (0.1 mL) and dioxane (1 mL). The mixture was sparged with N2 for 5 min and PdCl2(dppf) (4 mg, 0.005 mmol) was added. The mixture was sparged with N2 for 5 min and heated at 110° C. for 40 min in the microwave. The reaction mixture was filtered and the filtrate was purified by prep HPLC under acidic conditions, which led to loss of the t-butyl group, to afford the title compound (12.6 mg, 55%) as an oil. LC-MS Method 1 tR=1.27 min, m/z=448, 390; 1H NMR (CD3OD) 0.96 (s, 3H), 1.26 (s, 3H), 1.56 (d, 3H), 2.17 (s, 2H), 2.22 (m, 1H), 2.47 (m, 2H), 3.02 (m, 1H), 5.56 (q, 1H), 7.00 (d, 2H), 7.20-7.30 (5H), 7.58 (d, 2H), 7.77 (s, 1H), 8.14 (s, 1H).

Provenance & Evidence