Water → 2-Methyindole-4-carboxylic acid benzyl ester

HRID 11407Notes

Reaction equation

[CH3:1][C:2]1[NH:3][C:4]2[CH:5]=[CH:6][CH:7]=[C:8]([C:11]([OH:13])=[O:12])[C:9]=2[CH:10]=1.C(=O)([O-])[O-].[K+].[K+].[CH2:20](Br)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.O>CN(C)C=O.C(OCC)(=O)C>[CH2:20]([O:12][C:11]([C:8]1[C:9]2[CH:10]=[C:2]([CH3:1])[NH:3][C:4]=2[CH:5]=[CH:6][CH:7]=1)=[O:13])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

Conditions

Temperature: 80 °C

Procedure

To a solution of 2-methylindole-4-carboxylic acid (690 mg; prepared in Reference Example 10) in N,N-dimethylformamide (10 ml) was added anhydrous potassium carbonate (815 mg) and benzyl bromide (0.7 ml) at room temperature, and the mixture was stirred at 80° C. for 2 hours. To the reaction solution was added water and ethyl acetate, and then extracted. The aqueous layer was extracted with ethyl acetate. The combined organic layer was washed with water and a saturated aqueous solution of sodium chloride, successively, dried and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel (hexane-ethyl acetate) to give the title compound (610 mg) having the following physical data.

Workup

extractionextracted
extractionThe aqueous layer was extracted with ethyl acetate
washThe combined organic layer was washed with water
dry with materiala saturated aqueous solution of sodium chloride, successively, dried
concentrationconcentrated under reduced pressure
customThe residue was purified by column chromatography on silica gel (hexane-ethyl acetate)

Sources & evidence

ORD record: ord-8816db2c05c24d459c479b80e73fd217
Source dataset: uspto-grants-2006_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07098234B2

Reaction notes

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