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

HRID 1108690Notes

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 of 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 of ethyl acetate and hexane

Sources & evidence

ORD record: ord-a6d1f4ee788f4e61b53561608e6d1754
Source dataset: uspto-grants-2000_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06069156

Reaction notes

Loading…