6-Benzyloxy-4-methyl-1H-indole-2-carboxylic acid → 6-(benzyloxy)-4-methyl-1H-indole

HRID 915443Notes

Reaction equation

[CH2:1]([O:8][C:9]1[CH:17]=[C:16]2[C:12]([CH:13]=[C:14](C(O)=O)[NH:15]2)=[C:11]([CH3:21])[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>N1C2C(=CC=CC=2)C=CC=1.[Cr]([O-])([O-])=O.[Cu+2]>[CH2:1]([O:8][C:9]1[CH:17]=[C:16]2[C:12]([CH:13]=[CH:14][NH:15]2)=[C:11]([CH3:21])[CH:10]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

Conditions

Temperature: 230 °C

Procedure

A suspension of 6-benzyloxy-4-methyl-1H-indole-2-carboxylic acid (28 mg, 0.95 mmol) and copper chromite (19 mg, 0.06 mmol) in quinoline (1.4 ml) was heated at 230° C. (bath temp.) for 1.5 h. The mixture was poured onto 2 N HCl/ice water 1/1 and extracted three times with ethyl acetate. The combined extracts were washed with saturated aqueous NaHCO3 solution and brine and dried over sodium sulfate. Evaporation of the solvent under reduced pressure left a black oil which was purified by column chromatography (silica gel, n-heptane/AcOEt) to yield 90 mg (0.32 mmol, 34%) of the title compound as brown oil.

Workup

extractionextracted three times with ethyl acetate
washThe combined extracts were washed with saturated aqueous NaHCO3 solution and brine
dry with materialdried over sodium sulfate
customEvaporation of the solvent under reduced pressure
waitleft a black oil which
customwas purified by column chromatography (silica gel, n-heptane/AcOEt)

Sources & evidence

ORD record: ord-dadac9b9d37847db9bb4fbe42790d1cf
Source dataset: uspto-grants-2007_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07265149B2

Reaction notes

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