반응 #648757

반응 방정식

trifluoroacetic acid

compound

2-[1-(4-Chlorophenyl)-1-hydroxyethyl]cyclopropanecarbonitrile

compound

7-[(Methylsulfanyl)methyl]-1H-indole

indium(III) chloride

→

title compound

2-[1-(4-Chlorophenyl)-1-{7-[(methylsulfanyl)methyl]-1H-indol-3-yl}ethyl]cyclopropanecarbonitrile

용매

dichloromethane

dichloromethane

반응 조건

후처리

1. 1
   온도under reflux for 0.5 h
2. 2
   온도After cooling
3. 3
   workup.STIRRINGthe mixture was stirred
4. 4
   온도under reflux for 5 min
5. 5
   세척washed with saturated aqueous sodium bicarbonate solution, water and saturated aqueous sodium chloride solution
6. 6
   건조dried over magnesium sulfate
7. 7
   여과filtered
8. 8
   농축concentrated
9. 9
   기타The residue was purified by preparative HPLC (RP18 column; mobile phase: acetonitrile/water gradient with addition of 0.1% formic acid)

실험 절차

150 mg (0.68 mmol) of the compound from Example 75A and 120 mg (0.68 mmol) of the compound from Example 8A were introduced into 4 ml of dichloromethane at 0° C., 157 mg (0.71 mmol) of indium(III) chloride were added, and the mixture was stirred at RT for 1 h and under reflux for 0.5 h. After cooling, 0.05 ml (0.68 mmol) of trifluoroacetic acid was added, and the mixture was stirred under reflux for 5 min. It was diluted with dichloromethane, washed with saturated aqueous sodium bicarbonate solution, water and saturated aqueous sodium chloride solution, dried over magnesium sulfate, filtered and concentrated. The residue was purified by preparative HPLC (RP18 column; mobile phase: acetonitrile/water gradient with addition of 0.1% formic acid) to result in 117 mg (45% of theory) of the title compound as mixture of diastereomers.

출처