Ammonium Chloride → 5-[2-Amino-4-(4-bromo-phenylcarbamoyl)-phenylsulfanyl]-indole-1-carboxylic acid tert-butyl ester

HRID 883953Notes

Reaction equation

HRID 883953 reaction equation
[C:1]([O:5][C:6]([N:8]1[C:16]2[C:11](=[CH:12][C:13]([S:17][C:18]3[CH:23]=[CH:22][C:21]([C:24](=[O:33])[NH:25][C:26]4[CH:31]=[CH:30][C:29]([Br:32])=[CH:28][CH:27]=4)=[CH:20][C:19]=3[N+:34]([O-])=O)=[CH:14][CH:15]=2)[CH:10]=[CH:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[Cl-].[NH4+]>O.C(O)C.C(OCC)(=O)C.[Fe]>[C:1]([O:5][C:6]([N:8]1[C:16]2[C:11](=[CH:12][C:13]([S:17][C:18]3[CH:23]=[CH:22][C:21]([C:24](=[O:33])[NH:25][C:26]4[CH:27]=[CH:28][C:29]([Br:32])=[CH:30][CH:31]=4)=[CH:20][C:19]=3[NH2:34])=[CH:14][CH:15]=2)[CH:10]=[CH:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

7

Reactant 2

HCID 25517Ammonium ChlorideHCID 670409965-[4-(4-Bromo-phenylcarbamoyl)-2-nitro-phenylsulfanyl]-indole-1-carboxylic acid tert-butyl ester

Product 1

HCID 670407265-[2-Amino-4-(4-bromo-phenylcarbamoyl)-phenylsulfanyl]-indole-1-carboxylic acid tert-butyl esterYield 92%

Reagents, catalysts & solvents 4

HCID 23925IronCatalystHCID 702EthanolSolventHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

A suspension of the product of Example 59D (75 mg, 0.132 mmol), iron powder (45.3 mg, 0.811 mmol), and ammonium chloride (46 mg, 0.864 mmol) in water (1 mL) and ethanol (2 mL) was heated at 95° for 30 minutes. The reaction was cooled to room temperature, diluted with 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 by rotary evaporation under vacuum to afford the title compound as a yellow solid (65 mg, 92%).

Workup

  1. temperaturewas heated at 95° for 30 minutes
  2. washwashed with water (2×25 mL) and brine (25 mL)
  3. dry with materialThe organic phase was dried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated by rotary evaporation under vacuum

Sources & evidence

ORD record
ord-5a2ebedc63aa4428b1082c257f0a785e
Source dataset
uspto-grants-2012_08
Patent number
US08236950B2

Reaction notes

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