2-Bromopyridine → HCID 118497059, compound

Participants

Reaction Steps

To a solution of methyl 2-chloro-4-methoxy-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate in dioxane (Preparation 47, 935 mg, 2.86 mmol) was added 2M Na2CO3 (4.30 mL, 8.58 mmol) and stirred for 15 minutes at room temperature. 2-bromopyridine (542 mg, 3.43 mmol) was added and the reaction was purged with nitrogen for 15 minutes. Pd(dppf)Cl2 (117 mg, 0.14 mmol) was added and the reaction heated at 110° C. for 2 hours. The reaction was cooled to room temperature, filtered through arbocel and washed with EtOAc (50 mL). The filtrate was washed with brine (50 mL) and the aqueous layer was re-extracted with EtOAc (50 mL). The combined organic layers were dried over magnesium sulphate and concentrated in vacuo. The residue was purified using silica gel column chromatography eluting with 10-20% EtOAc in heptanes to afford the title compound (282 mg, 35% over 2 steps).

Provenance & Evidence