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

Temperatur

140 °C

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).

1. customThe reaction mixture was purged with argon
2. additionThe resultant mixture was diluted with water
3. extractionextracted with DCM (×2)
4. dry with materialthe organic phase was dried over sodium sulfate
5. filtrationfiltered
6. customthe solvent evaporated
7. customThe residue was purified by HPLC
8. washeluting with 10%-98% acetonitrile in water (0.1% formic acid) over 20 minutes
9. additionThe fractions containing the desired product
10. customwere freeze-dried

ORD-Eintrag

ord-b2a321dab17648a79ee019247f1b7d5a

Quelldatensatz

uspto-grants-2013_12

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US08614209B2