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

HRID 1989649Notes

Reaction equation

HRID 1989649 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])=[C:29]([O:37][CH3:38])[CH:28]=4)[CH:24]=[C:23]([CH3:39])[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>>[CH3:38][O:37][C:29]1[CH:28]=[C:27]([C:25]2[CH:24]=[C:23]([CH3:39])[N:22]=[C:21]([C:19]3[CH:18]=[CH:17][N:16]=[C:15]([C:11]4[CH:10]=[C:9]([S:6]([NH2:5])(=[O:7])=[O:8])[CH:14]=[CH:13][CH:12]=4)[CH:20]=3)[CH:26]=2)[CH:32]=[CH:31][C:30]=1[C:33]([F:36])([F:34])[F:35]

Participants

3

Reactant 2

HCID 6422Trifluoroacetic acidHCID 24759948N-tert-Butyl-3-[4-(3-methoxy-4-trifluoromethyl-phenyl)-6-methyl-[2,4']bipyridinyl-2'-yl]-benzenesulfonamide

Product 1

HCID 247599503-[4-(3-Methoxy-4-trifluoromethyl-phenyl)-6-methyl-[2,4']bipyridinyl-2'-yl]-benzenesulfonamideYield 100.1%

Conditions

Temperature
23 °C

Procedure

To N-tert-butyl-3-[4-(3-methoxy-4-trifluoromethyl-phenyl)-6-methyl-[2,4′]bipyridinyl-2′-yl]-benzenesulfonamide (example 336) (0.277 g, 0.5 mmol) was added TFA (3 mL) and the reaction mixture was stirred at 23° C. for 16 h. The mixture was evaporated to dryness and partitioned between EtOAc and saturated NaHCO3 solution, the organic layer was dried over Na2SO4. Removal of the solvent in vacuum left a crude product which was triturated with diethyl ether to give the title compound as a white solid (0.250 g, 100%). MS (ISP) 500.2 [(M+H)+]; mp 233° C. (dec.).

Workup

  1. customThe mixture was evaporated to dryness
  2. custompartitioned between EtOAc and saturated NaHCO3 solution
  3. dry with materialthe organic layer was dried over Na2SO4
  4. customRemoval of the solvent in vacuum
  5. waitleft a crude product which
  6. customwas triturated with diethyl ether

Sources & evidence

ORD record
ord-fa7e63e6fa8241af834803eef11f15b4
Source dataset
uspto-grants-2010_01
Patent number
US07642264B2

Reaction notes

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