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

HRID 874192ノート

反応式

HRID 874192 の反応式
[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

参加物

5

反応物 3

HCID 11430Potassium CarbonateHCID 4217082H-Tetrazole, 5-(trifluoromethyl)-, sodium salt (1:1)HCID 86660452methyl 4-(bromoacetyl)-1-(3-chloropyridin-2-yl)-1H-pyrrole-2-carboxylate

生成物 1

HCID 67125230methyl 1-(3-chloropyridin-2-yl)-4-{[5-(trifluoromethyl)-2H-tetrazol-2-yl]acetyl}-1H-pyrrole-2-carboxylate

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒2 回

反応条件

温度
70 °C

実験手順

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.

後処理

  1. temperatureheated
  2. temperatureat reflux for 15 min
  3. additionwere added
  4. distillationThe solvent was distilled off
  5. extractionthe mixture was extracted twice with dichloromethane
  6. washThe combined organic phases are washed with sodium chloride solution
  7. dry with materialdried over sodium sulphate
  8. concentrationconcentrated

出典と根拠

ORDレコード
ord-3829f007e77844899374cbe4c5c52549
出典データセット
uspto-grants-2015_03
特許番号
US08980886B2

反応ノート

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