Cesium carbonate → 4-(3-Trifluoromethyl-pyridin-2-yl)-1-[5-trifluoromethyl-1-(2-trimethylsilanyl-ethoxymethyl)-1H-benzoimidazol-2-yl]-piperazin-2-one

HRID 730828Notes

Reaction equation

HRID 730828 reaction equation
Cl[C:2]1[N:6]([CH2:7][O:8][CH2:9][CH2:10][Si:11]([CH3:14])([CH3:13])[CH3:12])[C:5]2[CH:15]=[CH:16][C:17]([C:19]([F:22])([F:21])[F:20])=[CH:18][C:4]=2[N:3]=1.[F:23][C:24]([F:39])([F:38])[C:25]1[C:26]([N:31]2[CH2:36][CH2:35][NH:34][C:33](=[O:37])[CH2:32]2)=[N:27][CH:28]=[CH:29][CH:30]=1.C1(P(C2C=CC=CC=2)C2C3OC4C(=CC=CC=4P(C4C=CC=CC=4)C4C=CC=CC=4)C(C)(C)C=3C=CC=2)C=CC=CC=1.C(=O)([O-])[O-].[Cs+].[Cs+]>O1CCOCC1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C(Cl)(Cl)Cl.[Pd].[Pd]>[F:39][C:24]([F:23])([F:38])[C:25]1[C:26]([N:31]2[CH2:36][CH2:35][N:34]([C:2]3[N:6]([CH2:7][O:8][CH2:9][CH2:10][Si:11]([CH3:14])([CH3:13])[CH3:12])[C:5]4[CH:15]=[CH:16][C:17]([C:19]([F:22])([F:21])[F:20])=[CH:18][C:4]=4[N:3]=3)[C:33](=[O:37])[CH2:32]2)=[N:27][CH:28]=[CH:29][CH:30]=1

Participants

7

Reactant 4

HCID 10796Cesium carbonateHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 471744384-(3-(Trifluoromethyl)pyridin-2-yl)piperazin-2-oneHCID 674013802-Chloro-5-trifluoromethyl-1-(2-trimethylsilanyl-ethoxymethyl)-1H-benzoimidazole

Product 1

HCID 865938294-(3-Trifluoromethyl-pyridin-2-yl)-1-[5-trifluoromethyl-1-(2-trimethylsilanyl-ethoxymethyl)-1H-benzoimidazol-2-yl]-piperazin-2-one

Reagents, catalysts & solvents 2

HCID 11029508Palladium, tris[mu-[(1,2-eta:4,5-eta)-(1E,4E)-1,5-diphenyl-1,4-pentadien-3-one]]di-, compd. with trichloromethane (1:1)CatalystHCID 312751,4-DioxaneSolvent

Procedure

A mixture of 2-chloro-5-trifluoromethyl-1-(2-trimethylsilanyl-ethoxymethyl)-1H-benzoimidazole from step (a) above (716 mg, 2 mmol), 4-(3-trifluoromethyl-pyridin-2-yl)-piperazin-2-one from step (b) above (500 mg, 2 mmol), tris (dibenzylideneacetone) dipalladium (0) chloroform adduct (207 mg, 0.2 mmol, Strem Chemicals), 4,5-bis (diphenylphosphino)-9,9-dimethylxanthene (213 mg, 0.4 mmol, Aldrich) and cesium carbonate (978 mg, 3 mmol, Aldrich) in 1,4-dioxane (2 mL) was subjected to microwave irradiation at 160° C. for 1.5 h. The mixture was cooled to room temperature, filtered, and the filtrate was purified by preparative HPLC (gradient 0.1% trifluoroacetic acid in acetonitrile) to give the title compound as a brown oil. MS (ESI, positive ion) m/z: 560 (M+1).

Workup

  1. customirradiation at 160° C. for 1.5 h
  2. filtrationfiltered
  3. customthe filtrate was purified by preparative HPLC (gradient 0.1% trifluoroacetic acid in acetonitrile)

Sources & evidence

ORD record
ord-fa524c6864664701bc6f8db49ec9b5db
Source dataset
uspto-grants-2009_09
Patent number
US07582761B2

Reaction notes

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