Toluene → 2-[4-(3-Methanesulfonyl-phenyl)-imidazol-1-yl]-4-trifluoromethyl-6-(4-trifluoromethylphenyl)-pyridine

HRID 1928372Notes

Reaction equation

HRID 1928372 reaction equation
C([Sn](CCCC)(CCCC)C1[N:7]=[CH:8][N:9]([C:11]2[CH:16]=[C:15]([C:17]([F:20])([F:19])[F:18])[CH:14]=[C:13]([C:21]3[CH:26]=[CH:25][C:24]([C:27]([F:30])([F:29])[F:28])=[CH:23][CH:22]=3)[N:12]=2)[CH:10]=1)CCC.BrC1C=C([CH2:46][S:47](CC2C=CC=C(Br)C=2)(=[O:49])=[O:48])C=CC=1.CCCCCCC.[C:65]1([CH3:71])[CH:70]=[CH:69][CH:68]=[CH:67][CH:66]=1>>[CH3:46][S:47]([C:67]1[CH:66]=[C:65]([C:71]2[N:7]=[CH:8][N:9]([C:11]3[CH:16]=[C:15]([C:17]([F:20])([F:19])[F:18])[CH:14]=[C:13]([C:21]4[CH:26]=[CH:25][C:24]([C:27]([F:30])([F:29])[F:28])=[CH:23][CH:22]=4)[N:12]=3)[CH:10]=2)[CH:70]=[CH:69][CH:68]=1)(=[O:49])=[O:48]

Participants

5

Reactant 4

HCID 1140Toluene2×HCID 8900HeptaneHCID 534433923-Bromophenylmethyl sulphoneHCID 574688332-(4-Tributylstannanyl-imidazol-1-yl)-4-trifluoromethyl-6-(4-trifluoromethyl-phenyl)-pyridine

Product 1

HCID 574690482-[4-(3-Methanesulfonyl-phenyl)-imidazol-1-yl]-4-trifluoromethyl-6-(4-trifluoromethylphenyl)-pyridineYield 29%

Procedure

A stirred mixture of 2-(4-tributylstannanyl-imidazol-1-yl)-4-trifluoromethyl-6-(4-trifluoromethyl-phenyl)-pyridine (Example G.11) (0.718 g, 1.0 mmol), commercially available 3-bromophenylmethyl sulfone (259 mg, 1.1 mmol), tetrakis(triphenyl-phosphine)palladium (0.058 g, 0.050 mmol) in toluene (5 mL) was heated under reflux conditions for 18 h. Cooled to rt, some precipitate occurred, diluted with toluene (˜5 mL), placed in freezer for 30 min, added heptane (total volume: 25 mL), filtered the precipitate off, washed with toluene/heptane (ca. 1:1, 3×10 mL), purified by silica gel column chromatography with heptane/ethyl acetate followed by trituration with diethyl ether/heptane to give the title compound as a white solid (0.150 g, 29%). MS (ISP) 512.3 [(M+H)+].

Workup

  1. temperaturewas heated under reflux conditions for 18 h
  2. filtrationfiltered the precipitate off,
  3. washwashed with toluene/heptane (ca. 1:1, 3×10 mL)
  4. custompurified by silica gel column chromatography with heptane/ethyl acetate

Sources & evidence

ORD record
ord-bb274d27744b4d8e985416223b1558da
Source dataset
uspto-grants-2012_05
Patent number
US08183262B2

Reaction notes

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