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

HRID 2374288Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2374288
[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]

Komponenten

8

Edukt 3

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

Produkt 1

HCID 59853697[5-Methanesulfonyl-2-(4-methyl-thiazol-2-yl)-phenyl]-[4-(4-trifluoromethyl-phenyl)-piperazin-1-yl]-methanoneAusbeute 25,4 %

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 83717Copper iodideKatalysatorHCID 6505921(1E,4E)-1,5-diphenylpenta-1,4-dien-3-one; palladiumKatalysatorHCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

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+.

Aufarbeitung

  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%)

Quellen und Nachweise

ORD-Eintrag
ord-65efc8f4cd9f4bf185307de29d959018
Quelldatensatz
uspto-grants-2008_12
Patentnummer
US07462617B2

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