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

HRID 883952

Reaction equation

HRID 883952 reaction equation
[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]

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

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%).

Workup

  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

Sources & evidence

ORD record
ord-d69c1fb25acb42a79c1b358340983ce4
Source dataset
uspto-grants-2012_08
Patent number
US08236950B2

Linked notes

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