Acetonitrile → 2-(1-(Methylsulfonyl)-1,2,3,6-tetrahydropyridin-4-yl)-5-((1-(2,2,2-trifluoroethyl)piperidin-4-yl)methoxy)pyridine

HRID 222598ノート

反応式

HRID 222598 の反応式
C(OC([N:8]1[CH2:13][CH2:12][CH:11]([CH2:14][O:15][C:16]2[CH:21]=C[C:19]([C:22]3[CH2:23][CH2:24][N:25]([S:28]([CH3:31])(=[O:30])=[O:29])[CH2:26][CH:27]=3)=[CH:18][C:17]=2F)[CH2:10][CH2:9]1)=O)(C)(C)C.C(=O)([O-])[O-].[K+].[K+].FC(F)(F)S(O[CH2:45][C:46]([F:49])([F:48])[F:47])(=O)=O.C(#[N:54])C>O>[CH3:31][S:28]([N:25]1[CH2:26][CH:27]=[C:22]([C:19]2[CH:18]=[CH:17][C:16]([O:15][CH2:14][CH:11]3[CH2:10][CH2:9][N:8]([CH2:45][C:46]([F:49])([F:48])[F:47])[CH2:13][CH2:12]3)=[CH:21][N:54]=2)[CH2:23][CH2:24]1)(=[O:30])=[O:29]

参加物

6

反応物 4

HCID 6342AcetonitrileHCID 11430Potassium CarbonateHCID 803662,2,2-Trifluoroethyl trifluoromethanesulfonateHCID 668644984-[2-Fluoro-4-(1-methanesulfonyl-1,2,3,6-tetrahydro-pyridin-4-yl)-phenoxymethyl]-piperidine-1-carboxylic acid tert-butyl ester

生成物 1

HCID 581111682-(1-(Methylsulfonyl)-1,2,3,6-tetrahydropyridin-4-yl)-5-((1-(2,2,2-trifluoroethyl)piperidin-4-yl)methoxy)pyridine

試薬・触媒・溶媒 1

HCID 962Water溶媒

反応条件

温度
85 °C

実験手順

To a solution of Preparation 6 (0.05 g, 0.14 mmol) in acetonitrile (1.50 mL) are added potassium carbonate (0.07 g, 0.56 mmol) and 2,2,2-trifluoroethyl trifluoromethanesulfonate (0.06 g, 0.28 mmol). The reaction mixture is heated at 85° C. for 1 h in a microwave, cooled to room temperature and diluted with water. The mixture is extracted with ethyl acetate and the combined organic extracts are dried over sodium sulfate, filtered, and concentrated. The residue is purified by flash column chromatography over silica gel to obtain 30 mg of the title compound as an off-white solid. MS (m/z) 433 (M+1).

後処理

  1. temperaturecooled to room temperature
  2. extractionThe mixture is extracted with ethyl acetate
  3. dry with materialthe combined organic extracts are dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue is purified by flash column chromatography over silica gel

出典と根拠

ORDレコード
ord-aec94733a5024d29887fcaa3cd68f965
出典データセット
uspto-grants-2012_06
特許番号
US08207344B2

反応ノート

読み込み中…