Trifluoro-methanesulfonic acid 6-methyl-4-(3-methyl-4-trifluoromethyl-phenyl)-pyridin-2-yl ester → N-tert-Butyl-3-[6'-methyl-4'-(3-methyl-4-trifluoromethyl-phenyl)-[2,2']bipyridinyl-6-yl]-benzenesulfonamide

HRID 1928482Notes

Reaction equation

HRID 1928482 reaction equation
[CH3:1][C:2]1[N:7]=[C:6](OS(C(F)(F)F)(=O)=O)[CH:5]=[C:4]([C:16]2[CH:21]=[CH:20][C:19]([C:22]([F:25])([F:24])[F:23])=[C:18]([CH3:26])[CH:17]=2)[CH:3]=1.[C:27]([NH:31][S:32]([C:35]1[CH:40]=[CH:39][CH:38]=[C:37]([C:41]2[CH:46]=[CH:45][CH:44]=[C:43]([Sn](CCCC)(CCCC)CCCC)[N:42]=2)[CH:36]=1)(=[O:34])=[O:33])([CH3:30])([CH3:29])[CH3:28]>C1(C)C=CC=CC=1>[C:27]([NH:31][S:32]([C:35]1[CH:40]=[CH:39][CH:38]=[C:37]([C:41]2[N:42]=[C:43]([C:6]3[CH:5]=[C:4]([C:16]4[CH:21]=[CH:20][C:19]([C:22]([F:24])([F:23])[F:25])=[C:18]([CH3:26])[CH:17]=4)[CH:3]=[C:2]([CH3:1])[N:7]=3)[CH:44]=[CH:45][CH:46]=2)[CH:36]=1)(=[O:33])=[O:34])([CH3:30])([CH3:28])[CH3:29]

Participants

4

Reactant 2

HCID 57468695Trifluoro-methanesulfonic acid 6-methyl-4-(3-methyl-4-trifluoromethyl-phenyl)-pyridin-2-yl esterHCID 60209340HCID 60209340, compound

Product 1

HCID 24760221N-tert-Butyl-3-[6'-methyl-4'-(3-methyl-4-trifluoromethyl-phenyl)-[2,2']bipyridinyl-6-yl]-benzenesulfonamide

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A stirred mixture of trifluoro-methanesulfonic acid 6-methyl-4-(3-methyl-4-trifluoromethyl-phenyl)-pyridin-2-yl ester (Example A.64) (0.250 g, 0.626 mmol), N-tert-butyl-3-(6-tributylstannanyl-pyridin-2-yl)-benzenesulfonamide (Example F.6) (0.363 g, 0.626 mmol), tetrakis(triphenyl-phosphine)palladium (0.036 g, 5 mol %) in toluene (5 mL) was heated under reflux conditions for 18 h. Removal of the solvent in vacuum left a crude product which was purified by silica gel column chromatography with n-heptane/ethyl acetate to give the title compound after trituration with diethyl ether as a white solid (300 mg, 88%). MS (ISP) 539.8 [(M+H)+]; mp 150° C. (dec.).

Workup

  1. temperaturewas heated under reflux conditions for 18 h
  2. customRemoval of the solvent in vacuum
  3. waitleft a crude product which
  4. customwas purified by silica gel column chromatography with n-heptane/ethyl acetate

Sources & evidence

ORD record
ord-969b299c601742e8890d5ab43454cdf8
Source dataset
uspto-grants-2012_05
Patent number
US08183262B2

Reaction notes

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