Heptane → 5-{1-[4-(3-methyl-4-trifluoromethyl-phenyl)-6-trifluoromethyl-pyrimidin-2-yl]-1H-imidazol-4-yl}-thiophene-2-sulfonic acid tert-butyl amide

HRID 1928228Notes

Reaction equation

HRID 1928228 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([C:12]2[CH:17]=[C:16]([C:18]([F:21])([F:20])[F:19])[N:15]=[C:14]([N:22]3[CH:26]=[C:25]([Sn](CCCC)(CCCC)CCCC)[N:24]=[CH:23]3)[N:13]=2)[CH:5]=[CH:6][C:7]=1[C:8]([F:11])([F:10])[F:9].[CH3:40][C:41]([NH:44][S:45]([C:48]1[S:52][C:51](Br)=[CH:50][CH:49]=1)(=[O:47])=[O:46])([CH3:43])[CH3:42].CCCCCCC>C1(C)C=CC=CC=1>[C:41]([NH:44][S:45]([C:48]1[S:52][C:51]([C:25]2[N:24]=[CH:23][N:22]([C:14]3[N:13]=[C:12]([C:4]4[CH:5]=[CH:6][C:7]([C:8]([F:11])([F:9])[F:10])=[C:2]([CH3:1])[CH:3]=4)[CH:17]=[C:16]([C:18]([F:21])([F:20])[F:19])[N:15]=3)[CH:26]=2)=[CH:50][CH:49]=1)(=[O:46])=[O:47])([CH3:43])([CH3:40])[CH3:42]

Participants

5

Reactant 3

HCID 8900HeptaneHCID 27571875-Bromo-N-tert-butylthiophene-2-sulfonamideHCID 574688314-(3-Methyl-4-trifluoromethyl-phenyl)-2-(4-tributylstannanyl-imidazol-1-yl)-6-trifluoromethyl-pyrimidine

Product 1

HCID 602094475-{1-[4-(3-methyl-4-trifluoromethyl-phenyl)-6-trifluoromethyl-pyrimidin-2-yl]-1H-imidazol-4-yl}-thiophene-2-sulfonic acid tert-butyl amideYield 81.4%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A stirred mixture of 4-(3-methyl-4-trifluoromethyl-phenyl)-2-(4-tributylstannanyl-imidazol-1-yl)-6-trifluoromethyl-pyrimidine (Example G.7) (0.33 g, 0.5 mmol), commercially available 5-bromothiophene-2-N-tert-butylsulfonamide (0.16 g, 0.55 mmol), tetrakis(triphenyl-phosphine)palladium (0.035 g, 0.03 mmol) in toluene (6 mL) was heated under reflux conditions for 15 h, heptane (10 mL) was added and the mixture was stirred at RT for 1 h. The precipitate was collected by filtration and dried to yield 5-{1-[4-(3-methyl-4-trifluoromethyl-phenyl)-6-trifluoromethyl-pyrimidin-2-yl]-1H-imidazol-4-yl}-thiophene-2-sulfonic acid tert-butyl amide (0.24 g) as a light yellow solid.

Workup

  1. temperaturewas heated under reflux conditions for 15 h
  2. filtrationThe precipitate was collected by filtration
  3. customdried

Sources & evidence

ORD record
ord-724ad252ce9442ea8b6064e0eb318d05
Source dataset
uspto-grants-2012_05
Patent number
US08183262B2

Reaction notes

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