Heptane → N-(2-Hydroxy-1,1-dimethyl-ethyl)-3-{1-[4-trifluoromethyl-6-(4-trifluoromethyl-phenyl)-pyridin-2-yl]-1H-imidazol-4-yl}-benzenesulfonamide

HRID 1989598Notes

Reaction equation

HRID 1989598 reaction equation
C([Sn](CCCC)(CCCC)[C:6]1[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.Br[C:40]1[CH:41]=[C:42]([S:46]([NH:49][C:50]([CH3:54])([CH3:53])[CH2:51][OH:52])(=[O:48])=[O:47])[CH:43]=[CH:44][CH:45]=1.CCCCCCC>C1(C)C=CC=CC=1>[OH:52][CH2:51][C:50]([NH:49][S:46]([C:42]1[CH:43]=[CH:44][CH:45]=[C:40]([C:6]2[N:7]=[CH:8][N:9]([C:11]3[CH:16]=[C:15]([C:17]([F:18])([F:19])[F:20])[CH:14]=[C:13]([C:21]4[CH:26]=[CH:25][C:24]([C:27]([F:29])([F:30])[F:28])=[CH:23][CH:22]=4)[N:12]=3)[CH:10]=2)[CH:41]=1)(=[O:48])=[O:47])([CH3:54])[CH3:53]

Participants

5

Reactant 3

HCID 8900HeptaneHCID 435019003-bromo-N-(2-hydroxy-1,1-dimethylethyl)benzenesulfonamideHCID 574688332-(4-Tributylstannanyl-imidazol-1-yl)-4-trifluoromethyl-6-(4-trifluoromethyl-phenyl)-pyridine

Product 1

HCID 57469033N-(2-Hydroxy-1,1-dimethyl-ethyl)-3-{1-[4-trifluoromethyl-6-(4-trifluoromethyl-phenyl)-pyridin-2-yl]-1H-imidazol-4-yl}-benzenesulfonamideYield 66%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

A stirred mixture of 2-(4-tributylstannanyl-imidazol-1-yl)-4-trifluoromethyl-6-(4-trifluoromethyl-phenyl)-pyridine (Example G.11) (0.503 g, 0.7 mmol), 3-bromo-N-(2-hydroxy-1,1-dimethyl-ethyl)-benzenesulfonamide (Example H.4) (0.237 g, 0.77 mmol), tetrakis(triphenyl-phosphine)palladium (0.040 g, 0.030 mmol) in toluene (5 mL) was heated under reflux conditions for 18 h. Cooled to rt, some precipitate occurred, diluted with toluene (˜5 mL), added heptane, filtered the precipitate off, washed with toluene/heptane, dried in HV to give the title compound as a white solid (268 mg, 66%). MS (ISP) 585.2 [(M+H)+]; mp 150° C. (dec.).

Workup

  1. temperaturewas heated under reflux conditions for 18 h
  2. filtrationfiltered the precipitate off,
  3. washwashed with toluene/heptane
  4. customdried in HV

Sources & evidence

ORD record
ord-aafad83a68ca40d99fa5205acd3ea7f8
Source dataset
uspto-grants-2010_01
Patent number
US07642264B2

Reaction notes

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