Ethyl 3-bromo-1-(3-(naphthalen-1-yloxy)propyl)-1h-indole-2-carboxylate → Ethyl 3-benzyl-1-(3-(naphthalen-1-yloxy)propyl)-1h-indole-2-carboxylate

HRID 1013285노트

반응식

HRID 1013285 반응식
Br[C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[N:4]([CH2:11][CH2:12][CH2:13][O:14][C:15]2[C:24]3[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=3)[CH:18]=[CH:17][CH:16]=2)[C:3]=1[C:25]([O:27][CH2:28][CH3:29])=[O:26].[Br-].[CH2:31]([Zn+])[C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1>C1COCC1.C(OCC)(=O)C>[CH2:31]([C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[N:4]([CH2:11][CH2:12][CH2:13][O:14][C:15]2[C:24]3[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=3)[CH:18]=[CH:17][CH:16]=2)[C:3]=1[C:25]([O:27][CH2:28][CH3:29])=[O:26])[C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1

참가 물질

5

반응물 2

HCID 67316935Ethyl 3-bromo-1-(3-(naphthalen-1-yloxy)propyl)-1h-indole-2-carboxylateHCID 178419772HCID 178419772, 화합물

생성물 1

HCID 67316098Ethyl 3-benzyl-1-(3-(naphthalen-1-yloxy)propyl)-1h-indole-2-carboxylate

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매2회HCID 8857Ethyl Acetate용매

실험 절차

A mixture of EXAMPLE 31C (100 mg), 0.5M benzyl zinc(II) bromide in THF (1.32 mL) and (1,1′-bis(diphenylphosphino)ferrocene)dichloropalladium(II) (18 mg) in THF (2 mL) was stirred at 60° C. for 16 hours. The mixture was diluted with ethyl acetate, and the organic phase was washed with water and brine and dried (MgSO4), filtered, and concentrated. The concentrate was purified by flash chromatography on silica gel with 0-8% ethyl acetate/hexanes.

후처리

  1. washthe organic phase was washed with water and brine
  2. dry with materialdried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe concentrate was purified by flash chromatography on silica gel with 0-8% ethyl acetate/hexanes

출처 및 근거

ORD 기록
ord-dc16410b960642219cfba2fbac0662ad
출처 데이터셋
uspto-grants-2011_07
특허 번호
US07981888B2

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