Pyridine → N-[1-Isopropyl-3-(3,4,5-trifluoro-phenyl)-1H-indol-6-yl]-methanesulfonamide

HRID 2079885노트

반응식

HRID 2079885 반응식
[NH2:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([C:14]3[CH:19]=[C:18]([F:20])[C:17]([F:21])=[C:16]([F:22])[CH:15]=3)=[CH:7][N:8]2[CH:11]([CH3:13])[CH3:12])=[CH:4][CH:3]=1.ClCCl.N1C=CC=CC=1.[CH3:32][S:33](Cl)(=[O:35])=[O:34]>C(OCC)(=O)C>[CH:11]([N:8]1[C:9]2[C:5](=[CH:4][CH:3]=[C:2]([NH:1][S:33]([CH3:32])(=[O:35])=[O:34])[CH:10]=2)[C:6]([C:14]2[CH:19]=[C:18]([F:20])[C:17]([F:21])=[C:16]([F:22])[CH:15]=2)=[CH:7]1)([CH3:13])[CH3:12]

참가 물질

6

반응물 4

HCID 1049PyridineHCID 6344DichloromethaneHCID 31297Methanesulfonyl chlorideHCID 574421936-amino-1-isopropyl-3-(3,4,5-trifluoro-phenyl)-1H-indole

생성물 1

HCID 67101228N-[1-Isopropyl-3-(3,4,5-trifluoro-phenyl)-1H-indol-6-yl]-methanesulfonamide수율 65.4%

시약·촉매·용매 1

HCID 8857Ethyl Acetate용매

실험 절차

Method I Combine 6-amino-1-isopropyl-3-(3,4,5-trifluoro-phenyl)-1H-indole (116.6 mg, 0.38 mmol), prepared as described immediately above, dichloromethane (3.0 mL) and pyridine (62 μL, 0.76 mmol) under a nitrogen atmosphere in a 25 mL flask. Cool the reaction to 0° C. and add methane sulfonyl chloride (33 μL, 0.42 mmol). Allow the reaction to warm to RT while stirring for 3 hours. Quench reaction with saturated aqueous sodium bicarbonate (5 mL), dilute with ethyl acetate (10 mL) and separate the layers. Wash the organic layer with water (5 mL), brine (5 mL), dry (Na2SO4) and filter. Concentrate the filtrate and adsorb the crude product onto silica gel. Purify by silica gel chromatography eluting with ethyl acetate in dichloromethane (0-5 v/v %) to give 95.1 mg of the title compound (61%). LRMS (API ES+)=383.0 (M+H).

후처리

  1. temperatureCool
  2. customthe reaction to 0° C.
  3. customthe reaction
  4. customQuench
  5. customreaction with saturated aqueous sodium bicarbonate (5 mL)
  6. customseparate the layers
  7. washWash the organic layer with water (5 mL), brine (5 mL)
  8. dry with materialdry (Na2SO4)
  9. filtrationfilter
  10. concentrationConcentrate the filtrate
  11. customPurify by silica gel chromatography
  12. washeluting with ethyl acetate in dichloromethane (0-5 v/v %)

출처 및 근거

ORD 기록
ord-8d02089631dd460189f2b6f46e7bc3d4
출처 데이터셋
uspto-grants-2011_04
특허 번호
US07932284B2

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