Thiophene-3-methanol → ethyl 2,3-dimethyl-1-(3-thienylmethyl)-1H-indole-5-carboxylate

HRID 1015435Notes

Reaction equation

[CH3:1][C:2]1[NH:3][C:4]2[C:9]([C:10]=1[CH3:11])=[CH:8][C:7]([C:12]([O:14][CH2:15][CH3:16])=[O:13])=[CH:6][CH:5]=2.[S:17]1[CH:21]=[CH:20][C:19]([CH2:22]O)=[CH:18]1>C1(C)C=CC=CC=1>[CH3:1][C:2]1[N:3]([CH2:22][C:19]2[CH:20]=[CH:21][S:17][CH:18]=2)[C:4]2[C:9]([C:10]=1[CH3:11])=[CH:8][C:7]([C:12]([O:14][CH2:15][CH3:16])=[O:13])=[CH:6][CH:5]=2

Participants

Conditions

Temperature: 110 °C

Procedure

A 500 mg portion of ethyl 2,3-dimethyl-1H-indole-5-carboxylate was dissolved in 24 ml of toluene, and 0.39 ml of 3-thienylmethanol and 1.00 g of cynomethylene tri-N-butylphospholan were added at room temperature, followed by overnight stirring at 110° C. A 0.39 ml portion of 3-thienylmethanol and 1.00 g of cyanomethylene tri-N-butylphospholan were added to the reaction liquid, followed by stirring at 110° C. for 8 hours. After evaporation of the solvent under a reduced pressure, the residue was purified by silica gel column chromatography (ethyl acetate:hexane=1:20 to 1:10) to obtain 378 mg of ethyl 2,3-dimethyl-1-(3-thienylmethyl)-1H-indole-5-carboxylate as a yellow solid.

Workup

stirringby stirring at 110° C. for 8 hours
customAfter evaporation of the solvent under a reduced pressure
customthe residue was purified by silica gel column chromatography (ethyl acetate:hexane=1:20 to 1:10)

Sources & evidence

ORD record: ord-20392d016cb942bba5dc79f6ccd10444
Source dataset: uspto-grants-2011_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07985764B2

Reaction notes

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