Sodium Carbonate → (R)-(2,2-dimethyl-1,3-dioxolan-4-yl)(6-(4-(4-fluorophenoxy)phenyl)pyridin-2-yl)methanone

Participants

Reaction Conditions

Reaction Steps

To a mixture of (R)-(6-bromopyridin-2-yl)(2,2-dimethyl-1,3-dioxolan-4-yl)methanone (0.574, g, 2.01, mmol) in dioxane (10, mL) was added 2-(4-(4-fluorophenoxyl)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (0.691, g, 2.20 mmol), 2M aqueous Na2CO3, (2.0, mL, 4.0, mmol), and PdCl2(dppf) (0.086, g, 0.11 mmol). The reaction vessel was flushed with argon, sealed, and heated at 100° C. for 3, hours. After cooling, the reaction mixture was evaporated in vacuo and the residue chromatographed over silica gel with 5-40% EtOAc in hexanes. The product fractions were evaporated in vacuo to give (R)-(2,2-dimethyl-1,3-dioxolan-4-yl)(6-(4-(4-fluorophenoxy)phenyl)pyridin-2-yl)methanone as a very pale tan thick oil (0.621, g, 1.58, mmol, 79% yield). LC/MS: m/z=394.2, [M+H]+, .

Provenance & Evidence