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

HRID 1928338Notes

Reaction equation

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

Participants

Reactant 2

HCID 6422Trifluoroacetic acid

HCID 68692928N-tert-Butyl-3-[4'-methyl-6'-(4-trifluoromethyl-phenyl)-[2,2']bipyridinyl-6-yl]-benzenesulfonamide

Product 1

HCID 686944243-[4'-Methyl-6'-(4-trifluoromethyl-phenyl)-[2,2']bipyridinyl-6-yl]-benzenesulfonamideYield 76%

Conditions

Temperature: 23 °C

Procedure

To N-tert-butyl-3-[4′-methyl-6′-(4-trifluoromethyl-phenyl)-[2,2′]bipyridinyl-6-yl]-benzenesulfonamide (example 299) (0.450 g, 0.856 mmol) was added TFA (5 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 an off-white solid (0.304 g, 76%). MS (ISP) 470.3 [(M+H)+]; mp 229° C.

Workup

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

Sources & evidence

ORD record: ord-df2647d590274f4b9b8395a37bc7e96b
Source dataset: uspto-grants-2012_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08183262B2

Reaction notes

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