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

HRID 1666489ノート

反応式

HRID 1666489 の反応式
[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

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-76038e813f34478394534a20e889856c
出典データセット
uspto-grants-2011_10
特許番号
US08044052B2

反応ノート

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