Water → Methyl 3-cyano-2-propylindole-6-carboxylate

HRID 278076Notes

Reaction equation

[CH2:1]([C:4]1[NH:5][C:6]2[C:11]([CH:12]=1)=[CH:10][CH:9]=[C:8]([C:13]([O:15][CH3:16])=[O:14])[CH:7]=2)[CH2:2][CH3:3].ClS([N:21]=[C:22]=O)(=O)=O.CN(C)C=O.O>C(#N)C>[C:22]([C:12]1[C:11]2[C:6](=[CH:7][C:8]([C:13]([O:15][CH3:16])=[O:14])=[CH:9][CH:10]=2)[NH:5][C:4]=1[CH2:1][CH2:2][CH3:3])#[N:21]

Participants

Conditions

Temperature: 0 °C

Procedure

To a stirred solution of methyl 2-propylindole-6-carboxylate (911 mg) in acetonitrile (15 ml) was added chlorosulfonylisocyanate (0.6 g) in acetonitrile (1.5 ml) at 0° C. The mixture was stirred at 0° C. for 30 minutes, then N,N-dimethylformamide (0.35 g) in acetonitrile (15 ml) was added at 0° C. The resultant mixture was stirred at 20° C. for 40 minutes, and then poured into water. The mixture was extracted with methylene chloride three times, and the combined organic phase was dried over sodium sulfate and evaporated in vacuo. The residue was chromatographed on silica gel eluting with a mixture of ethyl acetate and hexane (1:3) to give the crystals which were recrystallized from a mixture or ethyl acetate and hexane to give methyl 3-cyano-2-propylindole-6-carboxylate (535 mg) as colorless crystals.

Workup

extractionThe mixture was extracted with methylene chloride three times
dry with materialthe combined organic phase was dried over sodium sulfate
customevaporated in vacuo
customThe residue was chromatographed on silica gel eluting with a mixture of ethyl acetate and hexane (1:3)
customto give the crystals which
customwere recrystallized from a mixture or ethyl acetate and hexane

Sources & evidence

ORD record: ord-73641ddace5643e98885dc1764302b08
Source dataset: uspto-grants-2002_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06358992B1

Reaction notes

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