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

HRID 222598Notes

Reaction equation

HRID 222598 reaction equation
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]

Participants

6

Reactant 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

Product 1

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

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
85 °C

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-aec94733a5024d29887fcaa3cd68f965
Source dataset
uspto-grants-2012_06
Patent number
US08207344B2

Reaction notes

Loading…