Trifluoroacetic acid → 4-(2-Chlorophenyl)pyridin-3-amine

HRID 878126Notes

Reaction equation

HRID 878126 reaction equation
C(OC(=O)[NH:7][C:8]1[CH:9]=[N:10][CH:11]=[CH:12][C:13]=1[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[Cl:20])(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[Cl:20][C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][C:14]=1[C:13]1[CH:12]=[CH:11][N:10]=[CH:9][C:8]=1[NH2:7]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 70663564[4-(2-Chloro-phenyl)-pyridin-3-yl]-carbamic acid tert-butyl ester

Product 1

HCID 184033604-(2-Chlorophenyl)pyridin-3-amine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

An ice-cold solution of [4-(2-chloro-phenyl)-pyridin-3-yl]-carbamic acid tert-butyl ester (1.08 g, 3.54 mmol) in CH2Cl2 (11 mL) was treated with TFA (4.04 g, 2.73 mL) and stirred at room temperature for 3.5 hours. The volatiles were removed at a rotary evaporator and the residue taken up in CH2Cl2 and saturated aqueous NaHCO3 solution and the layers were separated. The aqueous layer was extracted twice with CH2Cl2 and the organic layers were washed with brine, dried over MgSO4, filtered, treated with silica gel and evaporated. The compound was purified by silica gel chromatography on a 10 g column using a MPLC system eluting with a gradient of n-heptane:EtOAc (100:0 to 0:100). Colorless solid (0.658 g, 90%). MS (ESI): m/z=205.05 [M+H]+.

Workup

  1. customThe volatiles were removed at a rotary evaporator
  2. customsaturated aqueous NaHCO3 solution and the layers were separated
  3. extractionThe aqueous layer was extracted twice with CH2Cl2
  4. washthe organic layers were washed with brine
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. additiontreated with silica gel
  8. customevaporated
  9. customThe compound was purified by silica gel chromatography on a 10 g column
  10. washeluting with a gradient of n-heptane:EtOAc (100:0 to 0:100)

Sources & evidence

ORD record
ord-80294afcc06647669c6741db9cfbd722
Source dataset
uspto-grants-2015_03
Patent number
US08987307B2

Reaction notes

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