Triphenylarsine → [5-Methanesulfonyl-2-(4-methyl-thiazol-2-yl)-phenyl]-[4-(4-trifluoromethyl-phenyl)-piperazin-1-yl]-methanone

HRID 2374288Notes

Reaction equation

HRID 2374288 reaction equation
[CH3:1][S:2]([C:5]1[CH:6]=[CH:7][C:8]([Sn](C)(C)C)=[C:9]([C:11]([N:13]2[CH2:18][CH2:17][N:16]([C:19]3[CH:24]=[CH:23][C:22]([C:25]([F:28])([F:27])[F:26])=[CH:21][CH:20]=3)[CH2:15][CH2:14]2)=[O:12])[CH:10]=1)(=[O:4])=[O:3].I[C:34]1[S:35][CH:36]=[C:37]([CH3:39])[N:38]=1.C1([As](C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>CN(C)C=O.O.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.[Pd].[Cu](I)I>[CH3:1][S:2]([C:5]1[CH:6]=[CH:7][C:8]([C:34]2[S:35][CH:36]=[C:37]([CH3:39])[N:38]=2)=[C:9]([C:11]([N:13]2[CH2:18][CH2:17][N:16]([C:19]3[CH:24]=[CH:23][C:22]([C:25]([F:28])([F:27])[F:26])=[CH:21][CH:20]=3)[CH2:15][CH2:14]2)=[O:12])[CH:10]=1)(=[O:4])=[O:3]

Participants

8

Reactant 3

HCID 11773TriphenylarsineHCID 231545942-Iodo-4-methyl-1,3-thiazoleHCID 59853642(5-Methanesulfonyl-2-trimethylstannanyl-phenyl)-[4-(4-trifluoromethyl-phenyl)-piperazin-1-yl]-methanone

Product 1

HCID 59853697[5-Methanesulfonyl-2-(4-methyl-thiazol-2-yl)-phenyl]-[4-(4-trifluoromethyl-phenyl)-piperazin-1-yl]-methanoneYield 25.4%

Reagents, catalysts & solvents 4

HCID 83717Copper iodideCatalystHCID 6505921(1E,4E)-1,5-diphenylpenta-1,4-dien-3-one; palladiumCatalystHCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of (5-Methanesulfonyl-2-trimethylstannanyl-phenyl)-[4-(4-trifluoromethyl-phenyl)-piperazin-1-yl]-methanone (Example T, 100 mg, 0.17 mmol), 2-Iodo-4-methyl-thiazole ( CAS: 34203-25-3; 43 mg, 0.19 mmol), Bis(dibenzylideneacetone)palladium (8 mg, 0.01 mmol), Triphenylarsine (25 mg, 0.08 mmol) and Copper iodide (3 mg, 0.02 mmol) in N,N-Dimethylformamide (2 ml) was heated at 100° C. for 1 hour. The mixture was cooled to room temperature, diluted with water, and extracted three times with Ethyl acetate. The combined organic phases were dried with Na2SO4 ,filtered, and evaporated to dryness. The residue was chromatographed over SiO2 (methanol/dichoromethane 0% to 0.5%) to provide the title compound (22 mg, 25%) as a light yellow solid. MS (ISP): 510.5 MH+.

Workup

  1. temperatureThe mixture was cooled to room temperature
  2. extractionextracted three times with Ethyl acetate
  3. dry with materialThe combined organic phases were dried with Na2SO4
  4. customevaporated to dryness
  5. customThe residue was chromatographed over SiO2 (methanol/dichoromethane 0% to 0.5%)

Sources & evidence

ORD record
ord-65efc8f4cd9f4bf185307de29d959018
Source dataset
uspto-grants-2008_12
Patent number
US07462617B2

Reaction notes

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