Sodium hydride → HCID 86674586, 화합물

HRID 2170657노트

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HRID 2170657 반응식
[CH3:1][C:2]1[NH:3][C:4]2[C:9]([C:10]=1[CH3:11])=[CH:8][C:7]([C:12]([O:14][CH2:15][CH:16]=[CH2:17])=[O:13])=[CH:6][CH:5]=2.[H-].[Na+].Br[CH2:21][C:22]1[CH:23]=[C:24]([CH:32]=[CH:33][C:34]=1[Cl:35])[O:25][C@@H:26]([CH3:31])[C:27]([O:29][CH3:30])=[O:28]>CN(C=O)C.CCOC(C)=O>[Cl:35][C:34]1[CH:33]=[CH:32][C:24]([O:25][C@@H:26]([CH3:31])[C:27]([O:29][CH3:30])=[O:28])=[CH:23][C:22]=1[CH2:21][N:3]1[C:4]2[C:9](=[CH:8][C:7]([C:12]([O:14][CH2:15][CH:16]=[CH2:17])=[O:13])=[CH:6][CH:5]=2)[C:10]([CH3:11])=[C:2]1[CH3:1]

참가 물질

6

반응물 3

HCID 24758Sodium hydrideHCID 27187797HCID 27187797, 화합물HCID 86674588HCID 86674588, 화합물

생성물 1

HCID 86674586HCID 86674586, 화합물

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

실험 절차

To a solution of the allyl 2,3-dimethyl-1H-indole-5-carboxylate (0.34 g, 1.483 mmol) in anhydrous DMF (3 mL) at 0° C. under argon protection was added NaH (0.08 g, 2.22 mmol). The mixture was stirred at rt for 30 min and re-cooled to 0° C., and then the (S)-methyl 2-(3-(bromomethyl)-4-chlorophenoxy)propanoate (0.55 g, 1.78 mmol) was added. The reaction was stirred at rt for another 1 h. The solvent was removed to obtain the crude, which was dissolved in EtOAc, then washed with water and brine and dried over Na2SO4. The solvent was removed to obtain the crude. The crude was purified by flash chromatography (AcOEt/Hexane 0-100%) to obtain the title compound. ESI-MS (m/z): 456 [M+1]+.

후처리

  1. temperaturere-cooled to 0° C.
  2. stirringThe reaction was stirred at rt for another 1 h
  3. customThe solvent was removed
  4. customto obtain the crude, which
  5. washwashed with water and brine
  6. dry with materialdried over Na2SO4
  7. customThe solvent was removed
  8. customto obtain the crude
  9. customThe crude was purified by flash chromatography (AcOEt/Hexane 0-100%)

출처 및 근거

ORD 기록
ord-523b7a85a4ed4bf6acbec41cb21c9a87
출처 데이터셋
uspto-grants-2015_06
특허 번호
US09051265B2

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