Lithium Chloride → (S)-1-[4-(4-fluorophenyl)-7-({4-[1-hydroxy-1-(trifluoromethyl)propyl]-1H-1,2,3-triazol-1-yl}methyl)quinolin-2-yl]ethanone

A mixture of (S)-2-(1-{[2-chloro-4-(4-fluorophenyl)quinolin-7-yl]methyl}-1H-1,2,3-triazol-4-yl)-1,1,1-trifluorobutan-2-ol (235 mg, 0.51 mmol), tributyl(1-ethoxyvinyl)tin (188 μL, 0.56 mmol), tetrakis(triphenylphosphine)palladium (30 mg, 0.025 mmol) and lithium chloride (64 mg, 1.5 mmol) was refluxed in dioxane (10 mL) overnight. An aqueous saturated solution of NaHCO3 was added and the mixture extracted with EtOAc. The combined organic layers were washed with brine, dried over Na2SO4 and concentrated under reduce pressure. THF (5 mL) and 3M HCl (2 mL) were added, and the solution was stirred at rt for 4 h. An aqueous saturated solution of NaHCO3 was added and the mixture extracted with EtOAc. The combined organic layers were washed with brine, dried over Na2SO4, filtered and concentrated under reduce pressure. Purification on silica gel (eluting with ethyl acetate/hexanes, 2:8) gave the title compound. MS (+ESI): 473 (M+H)+.

1. extractionthe mixture extracted with EtOAc
2. washThe combined organic layers were washed with brine
3. dry with materialdried over Na2SO4
4. concentrationconcentrated
5. additionTHF (5 mL) and 3M HCl (2 mL) were added
6. additionAn aqueous saturated solution of NaHCO3 was added
7. extractionthe mixture extracted with EtOAc
8. washThe combined organic layers were washed with brine
9. dry with materialdried over Na2SO4
10. filtrationfiltered
11. concentrationconcentrated
12. customPurification on silica gel (eluting with ethyl acetate/hexanes, 2:8)

ORDレコード

ord-376859a370dd48e7aeb1c0e59be5833e

出典データセット

uspto-grants-2011_06

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US07960409B2