Sodium Acetate → 5-[4-(4-Bromo-phenylcarbamoyl)-2-nitro-phenylsulfanyl]-indole-1-carboxylic acid tert-butyl ester

HRID 883952

반응식

HRID 883952 반응식
[C:1]([O:5][C:6]([N:8]1[C:16]2[C:11](=[CH:12][C:13]([SH:17])=[CH:14][CH:15]=2)[CH:10]=[CH:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[Br:18][C:19]1[CH:24]=[CH:23][C:22]([NH:25][C:26](=[O:37])[C:27]2[CH:32]=[CH:31][C:30](Cl)=[C:29]([N+:34]([O-:36])=[O:35])[CH:28]=2)=[CH:21][CH:20]=1.C([O-])(=O)C.[Na+]>C(O)C>[C:1]([O:5][C:6]([N:8]1[C:16]2[C:11](=[CH:12][C:13]([S:17][C:30]3[CH:31]=[CH:32][C:27]([C:26](=[O:37])[NH:25][C:22]4[CH:23]=[CH:24][C:19]([Br:18])=[CH:20][CH:21]=4)=[CH:28][C:29]=3[N+:34]([O-:36])=[O:35])=[CH:14][CH:15]=2)[CH:10]=[CH:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

참가 물질

5

반응물 3

HCID 517045Sodium AcetateHCID 1068537N-(4-bromophenyl)-4-chloro-3-nitrobenzamideHCID 670402485-Mercapto-indole-1-carboxylic acid tert-butyl ester

생성물 1

HCID 670409965-[4-(4-Bromo-phenylcarbamoyl)-2-nitro-phenylsulfanyl]-indole-1-carboxylic acid tert-butyl ester수율 85%

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

A solution of the product of Example 59C (39.9 mg, 0.160 mmol) in anhydrous ethanol (2 mL) under a nitrogen atmosphere was treated with the product of Example 49A (56.8 mg, 0.160 mmol) and anhydrous sodium acetate (66 mg, 0.800 mmol) at room temperature, then heated at reflux for 2 hours. The reaction was cooled to room temperature and the solvent removed by rotary evaporation under vacuum. The residue was taken up in ethyl acetate (50 mL) and washed with water (2×25 mL) and brine (25 mL). The organic phase was dried over anhydrous sodium sulfate, filtered, and concentrated under vacuum. Purification by silica gel flash chromatography using methylene chloride as eluent afforded the title compound as a yellow solid (77 mg, 85%).

후처리

  1. temperatureheated
  2. temperatureat reflux for 2 hours
  3. customthe solvent removed by rotary evaporation under vacuum
  4. washwashed with water (2×25 mL) and brine (25 mL)
  5. dry with materialThe organic phase was dried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under vacuum
  8. customPurification by silica gel flash chromatography

출처 및 근거

ORD 기록
ord-d69c1fb25acb42a79c1b358340983ce4
출처 데이터셋
uspto-grants-2012_08
특허 번호
US08236950B2

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