Ethyl Acetate → 2-Chloro-8-[6-(4-trifluoromethyl-phenyl)-pyrimidin-4-yloxy]-quinoline

HRID 858977노트

반응식

HRID 858977 반응식
Cl[C:2]1[CH:7]=[C:6]([C:8]2[CH:13]=[CH:12][C:11]([C:14]([F:17])([F:16])[F:15])=[CH:10][CH:9]=2)[N:5]=[CH:4][N:3]=1.[Cl:18][C:19]1[CH:28]=[CH:27][C:26]2[C:21](=[C:22]([OH:29])[CH:23]=[CH:24][CH:25]=2)[N:20]=1.C(=O)([O-])[O-].[K+].[K+].CCOC(C)=O>CN(C=O)C.[Cl-].[Na+].O>[Cl:18][C:19]1[CH:28]=[CH:27][C:26]2[C:21](=[C:22]([O:29][C:2]3[CH:7]=[C:6]([C:8]4[CH:13]=[CH:12][C:11]([C:14]([F:17])([F:16])[F:15])=[CH:10][CH:9]=4)[N:5]=[CH:4][N:3]=3)[CH:23]=[CH:24][CH:25]=2)[N:20]=1

참가 물질

7

반응물 4

HCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 2748782-Chloroquinolin-8-olHCID 167478374-Chloro-6-(4-(trifluoromethyl)phenyl)pyrimidine

생성물 1

HCID 100240132-Chloro-8-[6-(4-trifluoromethyl-phenyl)-pyrimidin-4-yloxy]-quinoline

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 57417360Sodium chloride; water용매

반응 조건

온도
90 °C

실험 절차

To a solution of 4-chloro-6-(4-trifluoromethyl-phenyl)-pyrimidine, (Example 2(a), Method A), (259 mg, 1 mmol) and 2-chloro-quinolin-8-ol (Example 2(a), Method B), (180 mg, 1 mmol) in 2 mL of DMF was added potassium carbonate (276 mg, 2 mmol). The reaction was stirred in a 90° C. oil bath for 2 h. EtOAc and brine were added, and the aqueous layer was extracted with EtOAc. The combined EtOAc layers were washed with brine, dried over Na2SO4, filtered, and concentrated in vacuum. Purification by flash chromatography by silica gel chromatography 1:4 of EtOAc/hexanes as eluent gave the title compound as a white solid. MS (ESI, pos. ion) m/z: 402 (M+1). Mp: 171.5–173.0° C. Anal. Calcd for C20H11ClF3N3O: C, 59.79; H, 2.76; N, 10.46. Found: C, 60.01; H, 2.80; N, 10.50.

후처리

  1. extractionthe aqueous layer was extracted with EtOAc
  2. washThe combined EtOAc layers were washed with brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuum
  6. customPurification by flash chromatography by silica gel chromatography 1:4 of EtOAc/hexanes as eluent

출처 및 근거

ORD 기록
ord-33d9b7ead4f14105829e812731489b23
출처 데이터셋
uspto-grants-2006_12
특허 번호
US07148221B2

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