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

HRID 2374288ノート

反応式

HRID 2374288 の反応式
[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]

参加物

8

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 4

HCID 83717Copper iodide触媒HCID 6505921(1E,4E)-1,5-diphenylpenta-1,4-dien-3-one; palladium触媒HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

反応条件

温度
100 °C

実験手順

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+.

後処理

  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%)

出典と根拠

ORDレコード
ord-65efc8f4cd9f4bf185307de29d959018
出典データセット
uspto-grants-2008_12
特許番号
US07462617B2

反応ノート

読み込み中…