Trifluoroacetic acid → 2-(3-(Fluoro(piperidin-4-ylidene)methyl)phenoxy)-5-(trifluoromethyl)pyridine

HRID 1666489

반응식

HRID 1666489 반응식
[F:1][C:2]([C:16]1[CH:21]=[CH:20][CH:19]=[C:18]([O:22][C:23]2[CH:28]=[CH:27][C:26]([C:29]([F:32])([F:31])[F:30])=[CH:25][N:24]=2)[CH:17]=1)=[C:3]1[CH2:8][CH2:7][N:6](C(OC(C)(C)C)=O)[CH2:5][CH2:4]1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[F:1][C:2](=[C:3]1[CH2:8][CH2:7][NH:6][CH2:5][CH2:4]1)[C:16]1[CH:17]=[C:18]([CH:19]=[CH:20][CH:21]=1)[O:22][C:23]1[CH:28]=[CH:27][C:26]([C:29]([F:31])([F:32])[F:30])=[CH:25][N:24]=1

참가 물질

4

반응물 2

HCID 6422Trifluoroacetic acidHCID 66876018Tert-butyl 4-(fluoro(3-(5-(trifluoromethyl)pyridin-2-yloxy)phenyl)methylene)piperidine-1-carboxylate

생성물 1

HCID 668762662-(3-(Fluoro(piperidin-4-ylidene)methyl)phenoxy)-5-(trifluoromethyl)pyridine수율 73.1%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To a solution of tert-butyl 4-(fluoro(3-(5-(trifluoromethyl)pyridin-2-yloxy)phenyl)methylene)piperidine-1-carboxylate (600 mg, 1.32 mmol) in CH2Cl2 (10 mL) was added TFA (0.98 mL, 13.26 mmol) dropwise maintaining ice-cooled conditions. The mixture was stirred for 1 h. The TFA was evaporated and the reaction mixture was partitioned between saturated NaHCO3 solution and CH2Cl2. The organic layer was dried over Na2SO4 and concentrated under reduced pressure to give the title compound (340 mg). 1H NMR (500 MHz, CDCl3): δ 2.3 (m, 2H), 2.6 (m, 2H), 2.8 (m, 2H), 2.9 (m, 2H), 7.0 (d, 1H, J=8.5 Hz), 7.1-7.4 (m, 4H), 7.9 (d, 1H, J=2 Hz), 8.4 (s, 1H).

후처리

  1. temperaturecooled conditions
  2. customThe TFA was evaporated
  3. customthe reaction mixture was partitioned between saturated NaHCO3 solution and CH2Cl2
  4. dry with materialThe organic layer was dried over Na2SO4
  5. concentrationconcentrated under reduced pressure

출처 및 근거

ORD 기록
ord-76038e813f34478394534a20e889856c
출처 데이터셋
uspto-grants-2011_10
특허 번호
US08044052B2

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