Trifluoroacetic acid → 5-(2-Fluoro-4-methanesulfonyl-phenyl)-2-piperidin-4-yl-furo[2,3-c]pyridine

HRID 1471768Notes

Reaction equation

HRID 1471768 reaction equation
FC(F)(F)C(O)=O.C(OC([N:15]1[CH2:20][CH2:19][CH:18]([C:21]2[O:40][C:24]3=[CH:25][N:26]=[C:27]([C:29]4[CH:34]=[CH:33][C:32]([S:35]([CH3:38])(=[O:37])=[O:36])=[CH:31][C:30]=4[F:39])[CH:28]=[C:23]3[CH:22]=2)[CH2:17][CH2:16]1)=O)(C)(C)C.C([O-])(O)=O.[Na+]>ClCCl>[F:39][C:30]1[CH:31]=[C:32]([S:35]([CH3:38])(=[O:37])=[O:36])[CH:33]=[CH:34][C:29]=1[C:27]1[CH:28]=[C:23]2[CH:22]=[C:21]([CH:18]3[CH2:19][CH2:20][NH:15][CH2:16][CH2:17]3)[O:40][C:24]2=[CH:25][N:26]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 516892Sodium BicarbonateHCID 679735964-[5-(2-Fluoro-4-methanesulfonyl-phenyl)-furo[2,3-c]pyridin-2-yl]-piperidine-1-carboxylic acid tert-butyl ester

Product 1

HCID 866945755-(2-Fluoro-4-methanesulfonyl-phenyl)-2-piperidin-4-yl-furo[2,3-c]pyridine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Trifluoroacetic acid (1.2 mL) is added to 4-[5-(2-fluoro-4-methanesulfonyl-phenyl)-furo[2,3-c]pyridin-2-yl]-piperidine-1-carboxylic acid tert-butyl ester (0.78 g) in dichloromethane (14 mL). The mixture is stirred at room temperature overnight. Aqueous NaHCO3 solution is added, the resulting mixture is stirred for 5 min, and the phases are separated. The aqueous phase is extracted with dichloromethane and the combined organic phases are washed with water and dried (Na2SO4). The solvent is evaporated to give the title compound. LC (method 1): tR=0.59 min; Mass spectrum (ESI+): m/z=375 [M+H]+.

Workup

  1. stirringthe resulting mixture is stirred for 5 min
  2. customthe phases are separated
  3. extractionThe aqueous phase is extracted with dichloromethane
  4. washthe combined organic phases are washed with water
  5. dry with materialdried (Na2SO4)
  6. customThe solvent is evaporated

Sources & evidence

ORD record
ord-a825771172d44fb8b737997021f612ab
Source dataset
uspto-grants-2015_04
Patent number
US09012456B2

Reaction notes

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