4-Phenyl-1H-indole → 2,4,6-Trimethyl-N-[2,2,2-trifluoro-1-(4-phenyl-1H-indol-3-ylmethyl)ethyl]benzenesulfonamide

HRID 1868423노트

반응식

HRID 1868423 반응식
[C:1]1([C:7]2[CH:15]=[CH:14][CH:13]=[C:12]3[C:8]=2[CH:9]=[CH:10][NH:11]3)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C([Mg]Br)C.[F:20][C:21]([F:38])([F:37])[CH:22]1[CH2:24][N:23]1[S:25]([C:28]1[C:33]([CH3:34])=[CH:32][C:31]([CH3:35])=[CH:30][C:29]=1[CH3:36])(=[O:27])=[O:26]>COC(C)(C)C.CCOCC.[Cu]I>[CH3:36][C:29]1[CH:30]=[C:31]([CH3:35])[CH:32]=[C:33]([CH3:34])[C:28]=1[S:25]([NH:23][CH:22]([CH2:24][C:9]1[C:8]2[C:12](=[CH:13][CH:14]=[CH:15][C:7]=2[C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[NH:11][CH:10]=1)[C:21]([F:38])([F:20])[F:37])(=[O:26])=[O:27]

참가 물질

7

반응물 3

HCID 158062984-Phenyl-1H-indoleHCID 574740362-Trifluoromethyl-1-(2,4,6-trimethylbenzenesulfonyl)aziridineHCID 178418443HCID 178418443, 화합물

생성물 1

HCID 116487802,4,6-Trimethyl-N-[2,2,2-trifluoro-1-(4-phenyl-1H-indol-3-ylmethyl)ethyl]benzenesulfonamide수율 44.5%

시약·촉매·용매 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)촉매HCID 3283Diethyl Ether용매HCID 15413tert-Butyl methyl ether용매2회

실험 절차

To a stirred solution of 115 mg (0.60 mmol) of 4-phenylindole in 2 mL of tert-butyl methyl ether at room temperature was added 0.25 mL (0.75 mmol) of a 3 M solution of ethyl magnesium bromide in ether. The mixture stirred for 30 minutes and then 22.8 mg (0.12 mmol) of copper (I) iodide was added. After 30 minutes, a solution of 87.9 mg (0.30 mmol) of 2-trifluoromethyl-1-(2,4,6-trimethylbenzenesulfonyl)aziridine in 1 mL of tert-butyl methyl ether was added. After 18 hours, the reaction was quenched with 1 mL of ice-cold water. After 10 minutes, the reaction mixture was diluted with dichloromethane, filtered through CELITE® filter aid, and concentrated in vacuo. The crude residue was purified by silica gel chromatography (12 g) eluting with ethyl acetate-hexanes (0-30% gradient) to afford an off-white solid. A second chromatography by preparative TLC eluting with ethyl acetate-hexanes (3:7) afforded 65 mg (22%) of the title compound as an off-white solid.

후처리

  1. waitAfter 30 minutes
  2. waitAfter 18 hours
  3. customthe reaction was quenched with 1 mL of ice-cold water
  4. waitAfter 10 minutes
  5. additionthe reaction mixture was diluted with dichloromethane
  6. filtrationfiltered through CELITE®
  7. filtrationfilter aid
  8. concentrationconcentrated in vacuo
  9. customThe crude residue was purified by silica gel chromatography (12 g)
  10. washeluting with ethyl acetate-hexanes (0-30% gradient)
  11. customto afford an off-white solid
  12. washA second chromatography by preparative TLC eluting with ethyl acetate-hexanes (3:7)

출처 및 근거

ORD 기록
ord-5845b3b2b58344b1b527c089bc24203c
출처 데이터셋
uspto-grants-2009_12
특허 번호
US07635711B2

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