1,4-Dioxane → 3-(4-fluoro-phenylmethyl)-1-methyl-1H-indole-5-carboxylic acid methyl ester

HRID 2195740

반응식

HRID 2195740 반응식
[CH3:1][O:2][C:3]([C:5]1[CH:6]=[C:7]2[C:11](=[CH:12][CH:13]=1)[N:10]([CH3:14])[CH:9]=[CH:8]2)=[O:4].[F:15][C:16]1[CH:23]=[CH:22][C:19]([CH2:20]Br)=[CH:18][CH:17]=1.O1CCOCC1>CCOCC>[CH3:1][O:2][C:3]([C:5]1[CH:6]=[C:7]2[C:11](=[CH:12][CH:13]=1)[N:10]([CH3:14])[CH:9]=[C:8]2[CH2:20][C:19]1[CH:22]=[CH:23][C:16]([F:15])=[CH:17][CH:18]=1)=[O:4]

참가 물질

5

반응물 3

HCID 312751,4-DioxaneHCID 680214-Fluorobenzyl bromide2회HCID 10679201Methyl 1-methyl-1H-indole-5-carboxylate

생성물 1

HCID 694495523-(4-fluoro-phenylmethyl)-1-methyl-1H-indole-5-carboxylic acid methyl ester수율 22%

시약·촉매·용매 1

HCID 3283Diethyl Ether용매

실험 절차

A solution of 1-methyl-1H-indole-5-carboxylic acid methyl ester (0.17 g, 0.9 mmol), prepared using procedures as described in Example 1, Ag2O (0.22 g, 0.95 mmol), 4-fluoro-benzyl bromide (0.18 g, 0.95 mmol) and dioxane (4 mL) were heated to reflux for 16 hr, then more 4-fluoro-benzyl bromide (90 mg, 0.5 mmol) was added and the solution was heated at reflux an additional 4 hr. After cooling to room temperature, the reaction mixture was diluted with ether (60 mL), washed with aq. NH4Cl (50 mL) and then brine (50 mL). The organic layer was dried over MgSO4, filtered and concentrated. The remaining residue was subjected to flash chromatography (ethyl acetate/hexane, 1:3) to provide 3-(4-fluoro-phenylmethyl)-1-methyl-1H-indole-5-carboxylic acid methyl ester (58 mg, 22% yield).

후처리

  1. temperaturewere heated
  2. temperatureto reflux for 16 hr
  3. temperaturethe solution was heated
  4. temperatureat reflux an additional 4 hr
  5. washwashed with aq. NH4Cl (50 mL)
  6. dry with materialThe organic layer was dried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated

출처 및 근거

ORD 기록
ord-191b2343760049c6955112d6e23c3b74
출처 데이터셋
uspto-grants-2012_12
특허 번호
US08338416B2

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