Potassium Carbonate → 7-(2-Fluoro-4-nitrophenoxy)-2-(1-methyl-1,2,3,6-tetrahydropyridin-4-yl)thieno[3,2-b]pyridine

Participants

Reaction Steps

To a mixture of the triflate 377 (450 mg, 1.84 mmol), bis(pinacolato)diboron (477 mg, 2.02 mmol) and K2CO3 (541 mg, 5.52 mmol) in DME (3.7 mg), Pd(PPh3)4 (106 mg, 0.092 mmol) was added in one portion and the system was heated to reflux for 2 h under N2. The reaction mixture was cooled and filtered. To the filtrate containing the intermediate 378 were added bromide 42 (435 mg, 1.84 mmol, scheme 8), CsF (838 mg, 5.52 mmol), NaHCO3 (463 mg, 5.52 mmol) and water (0.8 mL), and the mixture was heated to reflux for additional 2 h. It was then diluted with water and extracted with DCM; the organic solution was extracted with 1N HCl, the aqueous phase was basified to pH˜11 by addition of 2N aqueous NaOH, extracted with DCM; the extract was dried over anhydrous Na2SO4 and concentrated under reduced pressure affording 379 (279 mg, 39% yield) as a brown solid. LCMS:(M+H) 385.9.

Provenance & Evidence