Cesium carbonate → Methyl 7-[4-({[3-(2,6-dichlorophenyl)-5-(1-methylethyl)-4-isoxazolyl]methyl}oxy)phenyl]-2-naphthalenecarboxylate

HRID 1693672노트

반응식

HRID 1693672 반응식
Cl[CH2:2][C:3]1[C:4]([C:11]2[C:16]([Cl:17])=[CH:15][CH:14]=[CH:13][C:12]=2[Cl:18])=[N:5][O:6][C:7]=1[CH:8]([CH3:10])[CH3:9].[OH:19][C:20]1[CH:25]=[CH:24][C:23]([C:26]2[CH:35]=[C:34]3[C:29]([CH:30]=[CH:31][C:32]([C:36]([O:38][CH3:39])=[O:37])=[CH:33]3)=[CH:28][CH:27]=2)=[CH:22][CH:21]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C)C=O>[Cl:18][C:12]1[CH:13]=[CH:14][CH:15]=[C:16]([Cl:17])[C:11]=1[C:4]1[C:3]([CH2:2][O:19][C:20]2[CH:21]=[CH:22][C:23]([C:26]3[CH:35]=[C:34]4[C:29]([CH:30]=[CH:31][C:32]([C:36]([O:38][CH3:39])=[O:37])=[CH:33]4)=[CH:28][CH:27]=3)=[CH:24][CH:25]=2)=[C:7]([CH:8]([CH3:10])[CH3:9])[O:6][N:5]=1

참가 물질

5

반응물 3

HCID 10796Cesium carbonateHCID 592648754-(Chloromethyl)-3-(2,6-dichlorophenyl)-5-isopropylisoxazoleHCID 59264877Methyl 7-(4-hydroxyphenyl)-2-naphthalenecarboxylate

생성물 1

HCID 59264871Methyl 7-[4-({[3-(2,6-dichlorophenyl)-5-(1-methylethyl)-4-isoxazolyl]methyl}oxy)phenyl]-2-naphthalenecarboxylate수율 79.3%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

A solution of 4-(chloromethyl)-3-(2,6-dichlorophenyl)-5-(1-methylethyl)isoxazole (0.12 g, 0.36 mmol), methyl 7-(4-hydroxyphenyl)-2-naphthalenecarboxylate (0.084 g, 0.30 mmol), and cesium carbonate (137 mg, 0.42 mmol) in dimethylformamide (0.73 mL) was heated to 65° C. for 3 hours. The solution was partitioned between ethyl acetate and water. The organic layer was dried with magnesium sulfate, filtered and concentrated. The filtrate was purified by chromatography (silica gel, hexane to 3:7 ethyl acetate:hexanes) to provide the title compound (0.130 g, 68.4% as 1.0 ethyl acetate). 1H NMR (DMSO-d6): 8.66 (s, 1H), 8.34 (s, 1H), 8.04-8.00 (m, 2H), 7.94-7.90 (m, 2H), 7.69 (d, J=9 Hz, 2H), 7.62 (d, J=8 Hz, 2H), 7.55-7.51 (m, 1H), 6.91 (d, J=9 Hz, 2H), 4.87 (s, 2H), 3.90 (s, 3H), 3.46 (septet, J=7 Hz, 1H), 1.33 (d, J=7 Hz, 6H). ESI-LCMS m/z 546 (M+H)+.

후처리

  1. customThe solution was partitioned between ethyl acetate and water
  2. dry with materialThe organic layer was dried with magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe filtrate was purified by chromatography (silica gel, hexane to 3:7 ethyl acetate:hexanes)

출처 및 근거

ORD 기록
ord-254e9caeb5f6434b8cb9847d33725ea7
출처 데이터셋
uspto-grants-2012_04
특허 번호
US08158665B2

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