Sodium hydride → 7-[6-Phenyl-5-(4-trifluoromethyl-phenyl)-pyridazin-3-yloxy]-quinoline

HRID 859002노트

반응식

HRID 859002 반응식
Cl[C:2]1[N:7]=[N:6][C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[C:4]([C:14]2[CH:19]=[CH:18][C:17]([C:20]([F:23])([F:22])[F:21])=[CH:16][CH:15]=2)[CH:3]=1.[OH:24][C:25]1[CH:34]=[C:33]2[C:28]([CH:29]=[CH:30][CH:31]=[N:32]2)=[CH:27][CH:26]=1.[H-].[Na+]>CN(C=O)C>[C:8]1([C:5]2[N:6]=[N:7][C:2]([O:24][C:25]3[CH:34]=[C:33]4[C:28]([CH:29]=[CH:30][CH:31]=[N:32]4)=[CH:27][CH:26]=3)=[CH:3][C:4]=2[C:14]2[CH:19]=[CH:18][C:17]([C:20]([F:23])([F:22])[F:21])=[CH:16][CH:15]=2)[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

참가 물질

5

반응물 3

HCID 24758Sodium hydrideHCID 218651896-Chloro-3-phenyl-4-(4-trifluoromethyl-phenyl)-pyridazineHCID 1354268667-Hydroxyquinoline

생성물 1

HCID 218650647-[6-Phenyl-5-(4-trifluoromethyl-phenyl)-pyridazin-3-yloxy]-quinoline

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

반응 조건

온도
50 °C

실험 절차

To a solution of 6-chloro-3-phenyl-4-(4-trifluoromethyl-phenyl)-pyridazine, (Example 13 (e)), (106 mg, 0.3 mmol) and 7-hydroxyquinoline (55 mg, 0.4 mmol, Acros) in DMF (2.5 mL) was added NaH (22 mg, 0.6 mmol, 60% suspension in mineral oil, Aldrich) and the mixture was stired at room temperature for 15 h. The reaction mixture was then heated at 50° C. for another 28 h, allowed to cool to room temperature and the solvent removed in vacuum. The residue was partitioned between EtOAc/H2O and the aqueous layer was extracted with EtOAc. The combined organic layers were evaporated onto SiO2 and purified by flash silica gel chromatography with EtOAc/hexanes (0:1→3:7) as eluant to give the title compound as an off-white amorphous solid. Mp: 178–183° C. MS (ESI, pos ion.) m/z: 444 (M+1).

후처리

  1. temperatureto cool to room temperature
  2. customthe solvent removed in vacuum
  3. customThe residue was partitioned between EtOAc/H2O
  4. extractionthe aqueous layer was extracted with EtOAc
  5. customThe combined organic layers were evaporated onto SiO2
  6. custompurified by flash silica gel chromatography with EtOAc/hexanes (0:1→3:7) as eluant

출처 및 근거

ORD 기록
ord-18e33c20dad14892995dc3ff3fa0f3c5
출처 데이터셋
uspto-grants-2006_12
특허 번호
US07148221B2

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