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

HRID 2079885ノート

反応式

HRID 2079885 の反応式
[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]

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8857Ethyl Acetate溶媒

実験手順

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).

後処理

  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 %)

出典と根拠

ORDレコード
ord-8d02089631dd460189f2b6f46e7bc3d4
出典データセット
uspto-grants-2011_04
特許番号
US07932284B2

反応ノート

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