m-Fluorobenzenethiol → 1-(4-Fluoro-2-methylphenyl)-6-(3-fluorophenylthio)phthalazine

HRID 454868

反応式

HRID 454868 の反応式
Cl[C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8]([C:12]1[CH:17]=[CH:16][C:15]([F:18])=[CH:14][C:13]=1[CH3:19])=[N:7][N:6]=[CH:5]2.[F:20][C:21]1[CH:22]=[C:23]([SH:27])[CH:24]=[CH:25][CH:26]=1>CCN(CC)CC.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C(P[C-]1C=CC=C1)(C)C.[C-]1(PC(C)C)C=CC=C1.[Fe+2]>[F:18][C:15]1[CH:16]=[CH:17][C:12]([C:8]2[C:9]3[C:4](=[CH:3][C:2]([S:27][C:23]4[CH:24]=[CH:25][CH:26]=[C:21]([F:20])[CH:22]=4)=[CH:11][CH:10]=3)[CH:5]=[N:6][N:7]=2)=[C:13]([CH3:19])[CH:14]=1

参加物

6

反応物 2

HCID 75710m-FluorobenzenethiolHCID 667396776-Chloro-1-(4-fluoro-2-methylphenyl)phthalazine

生成物 1

HCID 452802411-(4-Fluoro-2-methylphenyl)-6-(3-fluorophenylthio)phthalazine

試薬・触媒・溶媒 3

HCID 167845palladium(II) acetate触媒HCID 1298591041,1'-Diisopropylphosphino ferrocene触媒HCID 8471Triethylamine溶媒

反応条件

温度
100 °C

実験手順

A mixture of 6-chloro-1-(4-fluoro-2-methylphenyl)phthalazine (0.197 g, 0.72 mmol), palladium(II) acetate (0.011 g, 0.049 mmol), 1,1′-bis(isopropylphosphino)ferrocene (0.022 g, 0.053 mmol) and 3-fluorothiophenol (0.080 ml, 0.95 mmol) in 2 mL of Et3N was sealed in a glass tube purged with argon and heated at 100° C. in an oil bath for 17 h. The reaction mixture was cooled to RT and diluted with MeOH. The solution was evaporated onto silica gel and purified by flash chromatography (ISCO 80 g column, eluting with 15-45% EtOAc in hexanes) to give the title compound as a white amorphous solid. MS (ESI, pos. ion) m/z: M+1=365.1

後処理

  1. customwas sealed in a glass tube
  2. custompurged with argon
  3. temperatureThe reaction mixture was cooled to RT
  4. additiondiluted with MeOH
  5. customThe solution was evaporated onto silica gel
  6. custompurified by flash chromatography (ISCO 80 g column, eluting with 15-45% EtOAc in hexanes)

出典と根拠

ORDレコード
ord-38a781dbc886467fa860b8024e980be1
出典データセット
uspto-grants-2013_07
特許番号
US08497269B2

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