Water → 5-(5-nitropyridin-2-yloxy)-1H-indole-2-carboxylic acid methyl ester

HRID 1038754Notes

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]([OH:14])=[CH:9][CH:8]=2)=[O:4].Cl[C:16]1[CH:21]=[CH:20][C:19]([N+:22]([O-:24])=[O:23])=[CH:18][N:17]=1.C(=O)([O-])[O-].[K+].[K+].O>CN(C=O)C>[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:16]1[CH:21]=[CH:20][C:19]([N+:22]([O-:24])=[O:23])=[CH:18][N:17]=1)=[CH:9][CH:8]=2)=[O:4]

Participants

Conditions

Temperature: 80 °C

Procedure

5-Hydroxy-1H-indole-2-carboxylic acid methyl ester (0.845 g, 4.42 mmol) and 2-chloro-5-nitropyridine (0.771 g, 4.86 mmol) were dissolved in DMF (5 mL). To the solution was added anhydrous potassium carbonate (0.611 g, 4.42 mmol) and the resulting solution was stirred for 18 hours at 80° C. Water (80 mL) was added to the reaction solution and the mixture was extracted with ethyl acetate (80 mL). The organic layer was washed with brine, dried over anhydrous sodium sulfate and the solvent was removed by evaporation. The residue was purified by silica gel column chromatography (AcOEt:n-hexane=1:3), then the obtained solid was recrystallized from ethyl acetate and n-hexane to yield 0.753 g of the title compound as a yellow powder.

Workup

extractionthe mixture was extracted with ethyl acetate (80 mL)
washThe organic layer was washed with brine
dry with materialdried over anhydrous sodium sulfate
customthe solvent was removed by evaporation
customThe residue was purified by silica gel column chromatography (AcOEt:n-hexane=1:3)
customthe obtained solid was recrystallized from ethyl acetate and n-hexane

Sources & evidence

ORD record: ord-145cb71ca4ac4cfd9b301e3e6a3ca599
Source dataset: uspto-grants-2013_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08551999B2

Reaction notes

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