Trifluoroacetic acid → 3-[6-Methyl-4-(4-trifluoromethyl-phenyl)-[2,4']bipyridinyl-2'-yl]-benzenesulfonamide

HRID 1989596Notes

Reaction equation

HRID 1989596 reaction equation
C([NH:5][S:6]([C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([C:15]2[CH:20]=[C:19]([C:21]3[CH:26]=[C:25]([C:27]4[CH:32]=[CH:31][C:30]([C:33]([F:36])([F:35])[F:34])=[CH:29][CH:28]=4)[CH:24]=[C:23]([CH3:37])[N:22]=3)[CH:18]=[CH:17][N:16]=2)[CH:10]=1)(=[O:8])=[O:7])(C)(C)C.C(O)(C(F)(F)F)=O>ClCCl>[CH3:37][C:23]1[N:22]=[C:21]([C:19]2[CH:18]=[CH:17][N:16]=[C:15]([C:11]3[CH:10]=[C:9]([S:6]([NH2:5])(=[O:8])=[O:7])[CH:14]=[CH:13][CH:12]=3)[CH:20]=2)[CH:26]=[C:25]([C:27]2[CH:32]=[CH:31][C:30]([C:33]([F:36])([F:34])[F:35])=[CH:29][CH:28]=2)[CH:24]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 24760814N-tert-Butyl-3-[6-methyl-4-(4-trifluoromethyl-phenyl)-[2,4']bipyridinyl-2'-yl]-benzenesulfonamide

Product 1

HCID 247608163-[6-Methyl-4-(4-trifluoromethyl-phenyl)-[2,4']bipyridinyl-2'-yl]-benzenesulfonamideYield 94%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred and cooled suspension of N-tert-butyl-3-[6-methyl-4-(4-trifluoromethylphenyl)-[2,4′]bipyridinyl-2′-yl]-benzenesulfonamide (example 287) (0.239 g, 0.455 mmol) in dichloromethane (1.5 mL) was added TFA (10 mL) and the reaction mixture was allowed to stir at room temperature for 16 h. The mixture was evaporated to dryness and saturated NaHCO3 solution (5 mL), diethyl ether and heptane were added. The mixture was stirred at room temperature for 1 h, the precipitate was collected by filtration, washed with water and heptane/diethyl ether and dried to yield the title compound as a white solid (0.200 g, 94%). MS (ISP) 470.3 [(M+H)+]; mp>250° C.

Workup

  1. temperaturecooled
  2. stirringto stir at room temperature for 16 h
  3. customThe mixture was evaporated to dryness and saturated NaHCO3 solution (5 mL), diethyl ether and heptane
  4. additionwere added
  5. stirringThe mixture was stirred at room temperature for 1 h
  6. filtrationthe precipitate was collected by filtration
  7. washwashed with water and heptane/diethyl ether
  8. customdried

Sources & evidence

ORD record
ord-058ab3fceb7e4dda8991beac87e61b97
Source dataset
uspto-grants-2010_01
Patent number
US07642264B2

Reaction notes

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