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

HRID 2374288노트

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HRID 2374288 반응식
[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]

참가 물질

8

반응물 3

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

생성물 1

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

시약·촉매·용매 4

HCID 83717Copper iodide촉매HCID 6505921(1E,4E)-1,5-diphenylpenta-1,4-dien-3-one; palladium촉매HCID 962Water용매HCID 6228Dimethylformamide용매

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온도
100 °C

실험 절차

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+.

후처리

  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%)

출처 및 근거

ORD 기록
ord-65efc8f4cd9f4bf185307de29d959018
출처 데이터셋
uspto-grants-2008_12
특허 번호
US07462617B2

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