Potassium Carbonate → methyl 1-(3-chloropyridin-2-yl)-4-{[5-(trifluoromethyl)-2H-tetrazol-2-yl]acetyl}-1H-pyrrole-2-carboxylate

HRID 874192Notes

Reaction equation

[F:1][C:2]([F:9])([F:8])[C:3]1[N:4]=[N:5][NH:6][N:7]=1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:17][C:18]([C:20]1[CH:21]=[C:22]([C:32]([O:34][CH3:35])=[O:33])[N:23]([C:25]2[C:30]([Cl:31])=[CH:29][CH:28]=[CH:27][N:26]=2)[CH:24]=1)=[O:19]>C(#N)C>[Cl:31][C:30]1[C:25]([N:23]2[CH:24]=[C:20]([C:18](=[O:19])[CH2:17][N:5]3[N:6]=[N:7][C:3]([C:2]([F:9])([F:8])[F:1])=[N:4]3)[CH:21]=[C:22]2[C:32]([O:34][CH3:35])=[O:33])=[N:26][CH:27]=[CH:28][CH:29]=1

Participants

Conditions

Temperature: 70 °C

Procedure

890 mg (1.61 mmol) of 5-(trifluoromethyl)-2H-tetrazole and 297 mg (2.14 mmol) of potassium carbonate were initially charged in 10 ml of acetonitrile and heated at reflux for 15 min. 630 mg (1.07 mmol) of methyl 4-(bromoacetyl)-1-(3-chloropyridin-2-yl)-1H-pyrrole-2-carboxylate, dissolved in 10 ml of acetonitrile, were added, and the reaction mixture was stirred at 70° C. for 1 h. The solvent was distilled off, the residue was taken up in water and the mixture was extracted twice with dichloromethane. The combined organic phases are washed with sodium chloride solution, dried over sodium sulphate and concentrated. The desired product was isolated by chromatographic purification.

Workup

temperatureheated
temperatureat reflux for 15 min
additionwere added
distillationThe solvent was distilled off
extractionthe mixture was extracted twice with dichloromethane
washThe combined organic phases are washed with sodium chloride solution
dry with materialdried over sodium sulphate
concentrationconcentrated

Sources & evidence

ORD record: ord-3829f007e77844899374cbe4c5c52549
Source dataset: uspto-grants-2015_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08980886B2

Reaction notes

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