3,5-Dibromopyridine → HCID 89486961, compound

Participants

Reaction Conditions

Reaction Steps

To a nitrogen degassed mixture of 3,5-dibromopyridine (4.61 g, 19.45 mmol), 2-(pyrrolidin-2-yl)thiazole (CA, 1.0 g, 6.48 mmol) and sodium t-butoxide (1.246 g, 12.97 mmol), in Toluene (20 ml) was added binap (0.807 g, 1.297 mmol) and tris(dibenzylideneacetone)di-palladium(0) (0.594 g, 0.648 mmol). The reaction was sealed and heated at 90° C. for 30 min. The reaction was cooled, quenched into water (100 mL), aqueous KHSO4 (20 mL) and ethyl acetate (200 mL) added. Aqueous NaHCO3 was added to adjust pH basic and ethyl acetate layer removed. Aqueous extract washed with ethyl acetate (50 mL) and the organic extracts washed with brine (50 mL), dried over sodium sulfate and concentrated to oil. The oil was chromatographed on silica using 25-75% ethyl acetate/hexanes to give 1.6 g foam of 1-7.

Provenance & Evidence