Water → 5-[5-(3,4-dichlorobenzoylamino)pyridin-2-yloxy]-1H-indole-2-carboxylic acid methyl ester

HRID 1038757Notes

Reaction equation

HRID 1038757 reaction equation
[CH3:1][O:2][C:3]([C:5]1[NH:6][C:7]2[C:12]([CH:13]=1)=[CH:11][C:10]([O:14][C:15]1[CH:20]=[CH:19][C:18]([N+:21]([O-])=O)=[CH:17][N:16]=1)=[CH:9][CH:8]=2)=[O:4].C(N(CC)CC)C.[Cl:31][C:32]1[CH:33]=[C:34]([CH:38]=[CH:39][C:40]=1[Cl:41])[C:35](Cl)=[O:36].O>C1COCC1.[Pd]>[CH3:1][O:2][C:3]([C:5]1[NH:6][C:7]2[C:12]([CH:13]=1)=[CH:11][C:10]([O:14][C:15]1[CH:20]=[CH:19][C:18]([NH:21][C:35](=[O:36])[C:34]3[CH:38]=[CH:39][C:40]([Cl:41])=[C:32]([Cl:31])[CH:33]=3)=[CH:17][N:16]=1)=[CH:9][CH:8]=2)=[O:4]

Participants

7

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 76403Benzoyl chloride, 3,4-dichloro-HCID 684941625-(5-nitropyridin-2-yloxy)-1H-indole-2-carboxylic acid methyl ester

Product 1

HCID 684953285-[5-(3,4-dichlorobenzoylamino)pyridin-2-yloxy]-1H-indole-2-carboxylic acid methyl esterYield 91.7%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

5-(5-Nitropyridin-2-yloxy)-1H-indole-2-carboxylic acid methyl ester (0.750 g, 2.39 mmol) was dissolved in THF (20 mL). To the solution was added 5% Pd/C (0.10 g), and the resulting mixture was subjected to catalytic reduction for 2 hours at room temperature under atmospheric pressure. The catalyst was removed by filtration, and the filtrate was concentrated to yield of a pale yellow oil (0.677 g). This product was dissolved in THF (30 mL). To the solution were added triethylamine (0.333 mL, 2.39 mmol), subsequently 3,4-Dichlorobenzoyl chloride (0.501 g, 2.39 mmol) and the resulting solution was stirred for 1 hour at room temperature. Water (30 mL) was added to the reaction solution, and the mixture was extracted with ethyl acetate (30 mL). After the organic layer was washed with brine, then dried over anhydrous sodium sulfate, the solvent was evaporated. The obtained residue was recrystallized from ethyl acetate to yield 1.00 g of the title compound as a white powder.

Workup

  1. customThe catalyst was removed by filtration
  2. concentrationthe filtrate was concentrated to yield of a pale yellow oil (0.677 g)
  3. dissolutionThis product was dissolved in THF (30 mL)
  4. extractionthe mixture was extracted with ethyl acetate (30 mL)
  5. washAfter the organic layer was washed with brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. customthe solvent was evaporated
  8. customThe obtained residue was recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-c24f0a862e684a7da8b3b5c98547181b
Source dataset
uspto-grants-2013_10
Patent number
US08551999B2

Reaction notes

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