Ethyl4-(1-(3,4-Difluorobenzylamino)-4,4-dimethyl-1,3-dioxopentan-2-yl)-3-nitrobenzoate → Ethyl2-tert-Butyl-3-(3,4-difluorobenzylcarbamoyl)-1H-indole-6-carboxylate

HRID 40114노트

반응식

HRID 40114 반응식
[CH2:1]([O:3][C:4](=[O:33])[C:5]1[CH:10]=[CH:9][C:8]([CH:11]([C:24](=O)[C:25]([CH3:28])([CH3:27])[CH3:26])[C:12]([NH:14][CH2:15][C:16]2[CH:21]=[CH:20][C:19]([F:22])=[C:18]([F:23])[CH:17]=2)=[O:13])=[C:7]([N+:30]([O-])=O)[CH:6]=1)[CH3:2]>CO.[NH4+].[Cl-].[Zn]>[C:25]([C:24]1[NH:30][C:7]2[C:8]([C:11]=1[C:12](=[O:13])[NH:14][CH2:15][C:16]1[CH:21]=[CH:20][C:19]([F:22])=[C:18]([F:23])[CH:17]=1)=[CH:9][CH:10]=[C:5]([C:4]([O:3][CH2:1][CH3:2])=[O:33])[CH:6]=2)([CH3:28])([CH3:27])[CH3:26]

참가 물질

5

반응물 1

HCID 59762433Ethyl4-(1-(3,4-Difluorobenzylamino)-4,4-dimethyl-1,3-dioxopentan-2-yl)-3-nitrobenzoate2회

생성물 1

HCID 59762341Ethyl2-tert-Butyl-3-(3,4-difluorobenzylcarbamoyl)-1H-indole-6-carboxylate

시약·촉매·용매 3

HCID 23994Zinc촉매HCID 887Methanol용매HCID 25517Ammonium Chloride용매

실험 절차

General Procedure R. To a solution of ethyl4-(1-(3,4-difluorobenzylamino)-4,4-dimethyl-1,3-dioxopentan-2-yl)-3-nitrobenzoate (Compound 114, 91 mg, 0.20 mmol) in MeOH (10 ml) and saturated aqueous NH4Cl (5 ml) was added zinc dust (320 mg, 4.9 mmol). The mixture was stirred at room temperature for 0.5 h, filtered and concentrated. The remaining aqueous suspension was extracted with EtOAc (×3). The combined organic layer was washed with brine, dried over Na2SO4, and concentrated in vacuo. The residue was purified by chromatography on silica gel (0→50% EtOAc-hexanes) to yield the title compound.

후처리

  1. filtrationfiltered
  2. concentrationconcentrated
  3. extractionThe remaining aqueous suspension was extracted with EtOAc (×3)
  4. washThe combined organic layer was washed with brine
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by chromatography on silica gel (0→50% EtOAc-hexanes)

출처 및 근거

ORD 기록
ord-e07e999b09bf429bae12abd21d92ba21
출처 데이터셋
uspto-grants-2013_09
특허 번호
US08524917B2

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