Potassium Carbonate → Ethyl 6-{3-[3,5-bis(trifluoromethyl)phenyl]-3-(trifluoromethyl)pyrrolidin-1-yl}-2-(trifluoro-methyl)nicotinate

HRID 2206921

反応式

HRID 2206921 の反応式
Cl[C:2]1[CH:7]=[CH:6][C:5]([C:8]([O:10][CH2:11][CH3:12])=[O:9])=[C:4]([C:13]([F:16])([F:15])[F:14])[N:3]=1.[F:17][C:18]([F:39])([F:38])[C:19]1[CH:20]=[C:21]([C:29]2([C:34]([F:37])([F:36])[F:35])[CH2:33][CH2:32][NH:31][CH2:30]2)[CH:22]=[C:23]([C:25]([F:28])([F:27])[F:26])[CH:24]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[F:27][C:25]([F:26])([F:28])[C:23]1[CH:22]=[C:21]([C:29]2([C:34]([F:37])([F:35])[F:36])[CH2:33][CH2:32][N:31]([C:2]3[CH:7]=[CH:6][C:5]([C:8]([O:10][CH2:11][CH3:12])=[O:9])=[C:4]([C:13]([F:16])([F:15])[F:14])[N:3]=3)[CH2:30]2)[CH:20]=[C:19]([C:18]([F:17])([F:38])[F:39])[CH:24]=1

参加物

5

反応物 3

HCID 11430Potassium CarbonateHCID 18374277Ethyl 6-chloro-2-(trifluoromethyl)nicotinateHCID 532621863-[3,5-Bis(trifluoromethyl)phenyl]-3-(trifluoromethyl)pyrrolidine

生成物 1

HCID 87160624Ethyl 6-{3-[3,5-bis(trifluoromethyl)phenyl]-3-(trifluoromethyl)pyrrolidin-1-yl}-2-(trifluoro-methyl)nicotinate収率 79.8%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
100 °C

実験手順

Ethyl 2-chloro-6-(trifluoromethyl)pyridin-5-carboxylate (0.95 g), 3-[3,5-bis-(trifluoromethyl)phenyl]-3-(trifluoromethyl)pyrrolidine (1.4 g) and potassium carbonate (0.7 g) were added to N,N-dimethylformamide (30 ml), and heated for 5 hours at 100° C. After cooling, the reaction mixture was poured in ice water and extracted with ethyl acetate. The organic layer was dried over magnesium sulfate, the solvent was distilled off under reduced pressure, and purified by silica gel column chromatography to obtain ethyl 6-{3-[3,5-bis-(trifluoromethyl)phenyl]-3-(trifluoromethyl)pyrrolidin-1-yl}-2-(trifluoromethyl)nicotinate (1.7 g).

後処理

  1. temperatureAfter cooling
  2. extractionextracted with ethyl acetate
  3. dry with materialThe organic layer was dried over magnesium sulfate
  4. distillationthe solvent was distilled off under reduced pressure
  5. custompurified by silica gel column chromatography

出典と根拠

ORDレコード
ord-34b76fd80a0f4bd6ac3756f67c70aef7
出典データセット
uspto-grants-2016_06
特許番号
US09375000B2

関連ノート

読み込み中…