Sodium hydride → methyl 2-(4-chlorophenyl)-2-(4-formyl-1H-indol-1-yl)acetate

HRID 1427257노트

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HRID 1427257 반응식
[NH:1]1[C:9]2[CH:8]=[CH:7][CH:6]=[C:5]([CH:10]=[O:11])[C:4]=2[CH:3]=[CH:2]1.[H-].[Na+].Br[CH:15]([C:20]1[CH:25]=[CH:24][C:23]([Cl:26])=[CH:22][CH:21]=1)[C:16]([O:18][CH3:19])=[O:17]>CN(C=O)C.CCOC(C)=O>[Cl:26][C:23]1[CH:22]=[CH:21][C:20]([CH:15]([N:1]2[C:9]3[C:4](=[C:5]([CH:10]=[O:11])[CH:6]=[CH:7][CH:8]=3)[CH:3]=[CH:2]2)[C:16]([O:18][CH3:19])=[O:17])=[CH:25][CH:24]=1

참가 물질

6

반응물 3

HCID 24758Sodium hydrideHCID 333703Indole-4-carboxaldehydeHCID 10777987Methyl 2-bromo-2-(4-chlorophenyl)acetate

생성물 1

HCID 86705047methyl 2-(4-chlorophenyl)-2-(4-formyl-1H-indol-1-yl)acetate

시약·촉매·용매 2

HCID 6228Dimethylformamide용매2회HCID 8857Ethyl Acetate용매

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온도
0 °C

실험 절차

To a solution of 1H-indole-4-carbaldehyde (2.0 g, 13.79 mmol) in DMF (50 mL) was added NaH (0.66 g, 16.55 mmol) at 0° C. After stirring for 30 min at 0° C., a solution of methyl 2-bromo-2-(4-chlorophenyl)-acetate (4.67 g, 17.92 mmol) in DMF (20 mL) was added dropwise. The reaction was allowed to warm to rt and stirred for an additional 1 hr. Then it was diluted with EtOAc (200 mL) and quenched with water. The organic layer was separated and washed with brine (50 mL), dried over Na2SO4, filtered and the solvent was removed in vacuo. The residue was purified via column chromatography (0-20% EtOAc/hexanes) to provide the title compound.

후처리

  1. temperatureto warm to rt
  2. stirringstirred for an additional 1 hr
  3. customquenched with water
  4. customThe organic layer was separated
  5. washwashed with brine (50 mL)
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. customthe solvent was removed in vacuo
  9. customThe residue was purified via column chromatography (0-20% EtOAc/hexanes)

출처 및 근거

ORD 기록
ord-8b48ad9519324559a723f178c789bb0c
출처 데이터셋
uspto-grants-2015_01
특허 번호
US08933113B2

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