Dimethylacetamide → HCID 118116230, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of (±)-4-(5-bromo-2-ethoxycarbonylmethoxy-phenyl)-6,7-dihydro-4H-thiazolo[5,4-c]pyridine-5-carboxylic acid tert-butyl ester (375 mg, 0.75 mmol, 1.00 eq.) in N,N-dimethylacetamide (1.5 mL), zinc cyanide (44 mg, 0.37 mmol, 0.50 eq.), tris(dibenzylideneacetone)dipalladium(0) (15 mg, 16 μmol, 0.02 eq.), 1,1′-bis-(diphenylphosphino)-ferrocene (11 mg, 20 μmol, 0.03 eq.) and poly(methylhydrosiloxane) (15 μL) were added in sequence. The resulting mixture was stirred at 150° C. under microwave irradiation for 30 min. To the previous mixture, zinc cyanide (44 mg, 0.37 mmol, 0.50 eq.), tris(dibenzylideneacetone)dipalladium(0) (15 mg, 16 μmol, 0.02 eq.), 1,1′-bis-(diphenylphosphino)-ferrocene (11 mg, 20 μmol, 0.03 eq.) and poly(methylhydrosiloxane) (15 μL) were added. The resulting mixture was stirred at 150° C. under microwave irradiation for 30 min. The reaction mixture was diluted with AcOEt and water was added. The layers were separated and the org. layer was dried over MgSO4, filtered over celite, and concentrated in vacuo. The residue, redissolved in DMF (4 mL) and formic acid (0.2 mL), was purified by prep. HPLC (column: Waters XBridge, 30×75 mm, 10 um, UV/MS, acidic conditions) and evaporated to give the title compound as a brown oil.

Provenance & Evidence