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 40114ノート

反応式

HRID 40114 の反応式
[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]

参加物

5

反応物 1

HCID 59762433Ethyl4-(1-(3,4-Difluorobenzylamino)-4,4-dimethyl-1,3-dioxopentan-2-yl)-3-nitrobenzoate2 回

生成物 1

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

試薬・触媒・溶媒 3

HCID 23994Zinc触媒HCID 887Methanol溶媒HCID 25517Ammonium Chloride溶媒

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-e07e999b09bf429bae12abd21d92ba21
出典データセット
uspto-grants-2013_09
特許番号
US08524917B2

反応ノート

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