Nitrogen → tert-Butyl 1-benzyl-6-(4-fluorophenyl)-1,2,3,4-tetrahydroquinolin-3-ylcarbamate

Temperatur

60 °C

(1-Benzyl-6-bromo-1,2,3,4-tetrahydroquinolin-3-yl)-carbamic acid tert-butyl ester (2.00 g, 4.79 mmol), prepared as described in Example 29A, 4-fluorophenyl-boronic acid (2.01 g, 14.37 mmol) and K2CO3 (2.65 g, 19.16 mmol) in a mixed solvent of THF (50 mL) and MeOH (25 mL) were stirred at RT for 30 min while N2 was allowed to bubble through the mixture, and then PXPd (258 mg, 0.48 mmol) was added. The reaction mixture was heated at 60° C. under N2 for 3 h. After cooling to RT, the solvent was stripped and the residue was diluted with H2O (60 mL) and CH2Cl2 (100 mL). The aqueous layer was extracted with CH2Cl2 (100 mL×3), and the combined organic extracts were washed with saturated aqueous NaCl (50 mL), dried (Na2SO4), filtered and concentrated. The resulting residue was chromatographed (silica gel) eluting with EtOAc (0-20%) in hexanes to give the title compound (1.11 g, 54%) as a white foam.

1. customto bubble through the mixture
2. additionPXPd (258 mg, 0.48 mmol) was added
3. temperatureAfter cooling to RT
4. additionthe residue was diluted with H2O (60 mL) and CH2Cl2 (100 mL)
5. extractionThe aqueous layer was extracted with CH2Cl2 (100 mL×3)
6. washthe combined organic extracts were washed with saturated aqueous NaCl (50 mL)
7. dry with materialdried (Na2SO4)
8. filtrationfiltered
9. concentrationconcentrated
10. customThe resulting residue was chromatographed (silica gel)
11. washeluting with EtOAc (0-20%) in hexanes

ORD-Eintrag

ord-7914193fa2b54362a959efcb494e1c38

Quelldatensatz

uspto-grants-2010_05

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US07709647B2