Potassium Phosphate, Tribasic → {5-[1-(2-Morpholin-4-yl-ethyl)-1H-pyrazol-4-yl]-thiophen-3-yl}-(octahydro-quinolin-1yl)-methanone formate

Participants

Reaction Conditions

Reaction Steps

cis-(5-Bromo-thiophen-3-yl)-(octahydro-quinolin-1-yl)-methanone (0.06 g, 0.18 mmol) was mixed with 4-{2-[4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-pyrazol-1-yl]-ethyl}-morpholine (0.062 g, 0.2 mmol), tricyclohexylphosphine (0.004 g, 0.01 mmol), potassium phosphate (0.047 g, 0.22 mmol) and tris(dibenzylideneacetone)dipalladium (0) (0.007 g, 0.008 mmol) in DME (2 mL), IMS (0.5 mL) and water (0.25 mL). The reaction mixture was purged with argon then heated by microwave irradiation to 140° C. for 20 minutes. The resultant mixture was diluted with water and extracted with DCM (×2) then the organic phase was dried over sodium sulfate, filtered and the solvent evaporated. The residue was purified by HPLC, eluting with 10%-98% acetonitrile in water (0.1% formic acid) over 20 minutes. The fractions containing the desired product were freeze-dried to give the title compound (0.029 g). LCMS m/z 429.25 [M+H]+ R.T.=7.03 min (Analytical Method 2).

Provenance & Evidence