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

HRID 2206921

반응식

HRID 2206921 반응식
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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

반응 조건

온도
100 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-34b76fd80a0f4bd6ac3756f67c70aef7
출처 데이터셋
uspto-grants-2016_06
특허 번호
US09375000B2

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