3,5-Dibromopyridine → HCID 117628625, compound

Participants

Reaction Conditions

Reaction Steps

To a nitrogen degassed mixture of 3,5-dibromopyridine (294 mg, 1.242 mmol), 8-methyl-3-(trifluoromethyl)-5,6,7,8-tetrahydroimidazo[1,2-a]pyrazine hydrochloride (CA, 100 mg, 0.414 mmol) and sodium t-butoxide (119 mg, 1.242 mmol), in Toluene (2 ml) was added BINAP (51.5 mg, 0.083 mmol) and tris(dibenzylideneacetone)dipalladium(0) (37.9 mg, 0.041 mmol). The reaction was sealed and heated at 90° C. for ½ hrs. LCMS (215 nM) showed the reaction complete. The reaction was cooled, quenched into water (10 mL) and aqueous. KHSO4 (2 mL) and ethyl acetate (25 mL) added. Aqueous NaHCO3 was added to adjust pH to 7.5 and the ethyl acetate layer removed. Aqueous layer washed with ethyl acetate (25 mL) and organic extracted combined, washed with brine (10 mL), dried over sodium sulfate and concentrated to an oil. Oil chromatographed on silica using 25-70% ethyl acetate/hexanes to give 71 mg product, I-6, as a foam.

Provenance & Evidence