Sodium Carbonate → HCID 17888045, compound

Participants

Reaction Conditions

Reaction Steps

Argon was bubbled for 15 min through a suspension of 1.11 ml (1.276 g, 10.0 mmol) 4-Chloropicoline, 2.798 g (20.0 mmol, 2.0 equiv.) of 4-Fluorophenylboronic acid, and 1.917 g (33.0 mmol, 3.3 equiv.) of KF in 20 ml of Dioxane. Then 155 mg (0.15 mmol, 1.5 mol %)Pd2(dba)3×CHCl3 and 104 ul (93 mg, 0.45 mmol, 4.5 mol %) Tri-tert-butylphosphine were added. The mixture was then stirred for 1 h under argon at 100° C. The reaction was worked up in the usual manner with diethylether, water, and sodium carbonate solution. The combined organic phases were washed with 30 ml of water, dried and concentrated in vaccuo to yield 2.5 g of a light yellow oil which was purified by flash chromatography (heptane/ethyl acetate 1:1) to yield the title compound (1.81 g, 97%) as a white solid, MS (ISP): m/e=188.3 (M+H)+.

Provenance & Evidence