Trifluoroacetic acid → [4-(2-Chloro-phenyl)-pyridin-3-yl]-(2,2,2-trifluoro-ethyl)-amine

HRID 878071Notes

Reaction equation

HRID 878071 reaction equation
C(OC(=O)[N:7]([C:13]1[CH:14]=[N:15][CH:16]=[CH:17][C:18]=1[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=1[Cl:25])[CH2:8][C:9]([F:12])([F:11])[F:10])(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[Cl:25][C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][C:19]=1[C:18]1[CH:17]=[CH:16][N:15]=[CH:14][C:13]=1[NH:7][CH2:8][C:9]([F:12])([F:10])[F:11]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 70663661[4-(2-Chloro-phenyl)-pyridin-3-yl]-(2,2,2-trifluoro-ethyl)-carbamic acid tert-butyl ester

Product 1

HCID 70663252[4-(2-Chloro-phenyl)-pyridin-3-yl]-(2,2,2-trifluoro-ethyl)-amine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of [4-(2-chloro-phenyl)-pyridin-3-yl]-(2,2,2-trifluoro-ethyl)-carbamic acid tert-butyl ester (120 mg, 310 μmol) in CH2Cl2 (2 mL) at 0° C. was added TFA (2 mL). The reaction mixture was stirred at room temperature for 2 hours and then concentrated under vacuum. The residue was extracted with 30 mL 10% aqueous NaHCO3 solution and 30 mL EtOAc. The layers were separated and the aqueous layer was extracted a second time with 30 mL EtOAc. The combined organic layers were washed with 30 mL brine, dried over MgSO4, filtered and concentrated under vacuum. Light yellow solid (79 mg, 89%). MS (ESI): m/z=287.055 [M+H]+.

Workup

  1. concentrationconcentrated under vacuum
  2. extractionThe residue was extracted with 30 mL 10% aqueous NaHCO3 solution and 30 mL EtOAc
  3. customThe layers were separated
  4. extractionthe aqueous layer was extracted a second time with 30 mL EtOAc
  5. washThe combined organic layers were washed with 30 mL brine
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-edcd39856e724c76bbc34199a3adbe12
Source dataset
uspto-grants-2015_03
Patent number
US08987307B2

Reaction notes

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