Potassium Carbonate → HCID 22179824, compound

Participants

Reaction Conditions

Reaction Steps

A solution of Example 12A (0.775 g. 3.0 mmol) and 4-tributylstannylpyridine(1.22 g, 3.3 mmol) in 1-methyl-2-pyrrolidinone (5 mL) was treated with Pd2(dba)3 (55 mg, 0.06 mmol), CuI (65 mg, 0.35 mmol), Ph3P (125 mg, 0,475 mmol) and K2CO3 (550 mg, 3.9 mmol), purged with argon, and stirred for 25 hours at 90° C. The reaction mixture was diluted with ethyl acetate (50 mL) and saturated aqueous potassium fluoride (10 mL), stirred 2 hoursr at room temperature, and filtered through a pad of diatomaceous earth (Celite®). The filtrate layers were separated and the organic phase was washed with water and brine, dried (Na2SO4), filtered, and concentrated. The concentrate was purified by flash column chromatography on silica gel with 4:1 ethyl acetate and hexanes to provide 200 mg (36%) of the desired product. MS(ESI) m/e 188.1 (M+H)+.

Provenance & Evidence