Water → Ethyl 6-[4-({[3-(2,6-dichlorophenyl)-5(1-methylethyl)-4-isoxazolyl]methyl}oxy)phenyl]-7-fluoro-2-quinolinecarboxylate

HRID 2423500노트

반응식

HRID 2423500 반응식
C(=O)([O-])[O-].[Cs+].[Cs+].[F:7][C:8]1[CH:17]=[C:16]2[C:11]([CH:12]=[CH:13][C:14]([C:18]([O:20][CH2:21][CH3:22])=[O:19])=[N:15]2)=[CH:10][C:9]=1[C:23]1[CH:28]=[CH:27][C:26]([OH:29])=[CH:25][CH:24]=1.Cl[CH2:31][C:32]1[C:33]([C:40]2[C:45]([Cl:46])=[CH:44][CH:43]=[CH:42][C:41]=2[Cl:47])=[N:34][O:35][C:36]=1[CH:37]([CH3:39])[CH3:38].O>CN(C)C=O>[Cl:46][C:45]1[CH:44]=[CH:43][CH:42]=[C:41]([Cl:47])[C:40]=1[C:33]1[C:32]([CH2:31][O:29][C:26]2[CH:25]=[CH:24][C:23]([C:9]3[CH:10]=[C:11]4[C:16](=[CH:17][C:8]=3[F:7])[N:15]=[C:14]([C:18]([O:20][CH2:21][CH3:22])=[O:19])[CH:13]=[CH:12]4)=[CH:28][CH:27]=2)=[C:36]([CH:37]([CH3:39])[CH3:38])[O:35][N:34]=1

참가 물질

6

반응물 4

HCID 962WaterHCID 10796Cesium carbonateHCID 592648754-(Chloromethyl)-3-(2,6-dichlorophenyl)-5-isopropylisoxazoleHCID 59321502Ethyl 7-fluoro-6-(4-hydroxyphenyl)-2-quinolinecarboxylate

생성물 1

HCID 59321487Ethyl 6-[4-({[3-(2,6-dichlorophenyl)-5(1-methylethyl)-4-isoxazolyl]methyl}oxy)phenyl]-7-fluoro-2-quinolinecarboxylate수율 49%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

Cesium carbonate (62.6 mg, 192.2 μmol) was added to ethyl 7-fluoro-6-(4-hydroxyphenyl)-2-quinolinecarboxylate (54.4 mg, 174.7 μmol) and 4-(chloromethyl)-3-(2,6-dichlorophenyl)-5-(1-methylethyl)isoxazole (58.6 mg, 192.2 μmol) in N,N-dimethylformamide (1.7 mL) at room temperature. The resulting suspension was stirred for 68 hours, then water was added and the reaction mixture was extracted with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate, then filtered and concentrated. The residue was purified by silica gel chromatography eluting with 3:7 ethyl acetate:hexanes to give 49.4 mg (49%) of ethyl 6-[4-({[3-(2,6-dichlorophenyl)-5-(1-methylethyl)-4-isoxazolyl]methyl}oxy)phenyl]-7-fluoro-2-quinolinecarboxylate as an oil. 1H NMR (400 MHz, d6-DMSO): δ 8.61 (d, J=9 Hz, 1H), 8.23 (d, J=9 Hz, 1H), 8.11 (d, J=9 Hz, 1H), 8.02 (d, J=12 Hz, 1H), 7.65-7.62 (m, 2H), 7.56 (d, J=7 Hz, 2H), 7.56-7.52 (m, 1H), 6.96 (d, J=9 Hz, 2H), 4.90 (s, 2H), 4.42 (q, J=7 Hz, 2H), 3.48 (septet, J=7 Hz, 1H), 1.38 (t, J=7 Hz, 3H), 1.34 (d, J=7 Hz, 6H). ESI-LCMS m/z 579 (M+H)+.

후처리

  1. extractionthe reaction mixture was extracted with ethyl acetate
  2. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe residue was purified by silica gel chromatography
  6. washeluting with 3:7 ethyl acetate

출처 및 근거

ORD 기록
ord-21acd6b923c042559d6f9aa979c2c73a
출처 데이터셋
uspto-grants-2011_06
특허 번호
US07960552B2

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