Acetate → HCID 67811854, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of (3-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)isoxazol-5-yl)methyl acetate (0.865 g, 3.08 mmol) and (2-bromo-4,5-dimethylthiophen-3-yl)(4-chlorophenyl)methanone (0.534 g, 1.619 mmol) in 1,4-dioxane (7 mL) and water (2 mL) was added PdCl2(dppf)-CH2Cl2 adduct (0.090 g, 0.110 mmol) and K2CO3 (0.560 g, 4.05 mmol). The bi-phasic mixture was heated to 95° C. under a constant stream of N2 (g). After 5 h, the mixture was cooled to 45° C. and aqueous 1 N NaOH (4.0 mL, 4.00 mmol) was introduced. After an additional 1 h, LC-MS analysis shows complete conversion of acetate to alcohol. The mixture was cooled to room temperature, 1 N HCl was added to acidify the aqueous layer (pH ˜1) and the aqueous layer extracted MTBE (2×). The combined organic layer was washed with saturated NaHCO3, brine, dried over Na2SO4, and concentrated to give a dark brown oil. The oil was diluted with MTBE and stirred over activated charcoal for 15 min, then filtered over a plug of silica and Celite. The filter cake was washed with MTBE (2×) and subsequently concentration gave a brown oil. The resultant oil was purified on Biotage system (gradient elution 5% EtOAc:95% Hexanes to 40% EtOAc:60% Hexanes) to give the titled compound as a yellow oil (0.463 g, 1.28 mmol, 79% yield). LC/MS m/z 362 [M+H]+.

Provenance & Evidence