Trifluoroacetic acid → 3-[6-Methyl-4-(4-trifluoromethyl-phenyl)-[2,3']bipyridinyl-5'-yl]-benzenesulfonamide

HRID 1928323Notes

Reaction equation

HRID 1928323 reaction equation
C([NH:5][S:6]([C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([C:15]2[CH:16]=[C:17]([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]=[N:19][CH:20]=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:17]2[CH:18]=[N:19][CH:20]=[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:16]=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 24760815N-tert-Butyl-3-[6-methyl-4-(4-trifluoromethyl-phenyl)-[2,3']bipyridinyl-5'-yl]-benzenesulfonamide

Product 1

HCID 247608913-[6-Methyl-4-(4-trifluoromethyl-phenyl)-[2,3']bipyridinyl-5'-yl]-benzenesulfonamideYield 97%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred and cooled suspension of N-tert-butyl-3-[6-methyl-4-(4-trifluoromethyl-phenyl)-[2,3′]bipyridinyl-5′-yl]-benzenesulfonamide (example 288) (0.150 g, 0.29 mmol) in dichloromethane (0.9 mL) was added TFA (6.3 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 (0.130 g, 97%). MS (ISP) 470.3 [(M+H)+]; mp 235° C. (dec.).

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-2b023f7c469947fd854a6b72deeb77a0
Source dataset
uspto-grants-2012_05
Patent number
US08183262B2

Reaction notes

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