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

HRID 454868

반응식

HRID 454868 반응식
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

참가 물질

6

반응물 2

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

생성물 1

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

시약·촉매·용매 3

HCID 167845palladium(II) acetate촉매HCID 1298591041,1'-Diisopropylphosphino ferrocene촉매HCID 8471Triethylamine용매

반응 조건

온도
100 °C

실험 절차

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

후처리

  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)

출처 및 근거

ORD 기록
ord-38a781dbc886467fa860b8024e980be1
출처 데이터셋
uspto-grants-2013_07
특허 번호
US08497269B2

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