Ethyl Acetate → 3-[4-(4',5'-Difluoro-2'-methoxy-biphenyl-4-yloxymethyl)-indazol-1-yl]-propionic acid ethyl ester
반응식
[F:1][C:2]1[C:7]([F:8])=[CH:6][C:5]([C:9]2[CH:14]=[CH:13][C:12]([O:15][CH2:16][C:17]3[CH:25]=[CH:24][CH:23]=[C:22]4[C:18]=3[CH:19]=[N:20][NH:21]4)=[CH:11][CH:10]=2)=[C:4]([O:26][CH3:27])[CH:3]=1.Br[CH:29]([CH3:35])[C:30]([O:32][CH2:33][CH3:34])=[O:31].C(=O)([O-])[O-].[Cs+].[Cs+].CCOC(C)=O>CN(C=O)C.O>[CH2:33]([O:32][C:30](=[O:31])[CH2:29][CH2:35][N:21]1[C:22]2[C:18](=[C:17]([CH2:16][O:15][C:12]3[CH:11]=[CH:10][C:9]([C:5]4[CH:6]=[C:7]([F:8])[C:2]([F:1])=[CH:3][C:4]=4[O:26][CH3:27])=[CH:14][CH:13]=3)[CH:25]=[CH:24][CH:23]=2)[CH:19]=[N:20]1)[CH3:34]참가 물질
7
반응물 4
생성물 1
시약·촉매·용매 2
반응 조건
- 온도
- 90 °C
실험 절차
4-(4′,5′-Difluoro-2′-methoxy-biphenyl-4-yloxymethyl)-1H-indazole (0.09 g, 0.245 mmol), ethyl bromopropionate (0.045 g, 0.245 mmol), cesium carbonate (81 mg, 0.294 mmol) in 6 mL DMF was stirred at RT overnight and then heated to 90° C. for 35 min. The reaction was cooled and distributed between EtOAc and H2O. The organic layer was separated and concentrated in vacuo. The crude product was purified by flash chromatography with a gradient from 0-30% ethyl acetate in hexanes to yield 3-[4-(4′,5′-difluoro-2′-methoxy-biphenyl-4-yloxymethyl)-indazol-1-yl]-propionic acid ethyl ester as a white solid (98 mg, 85.7%).
후처리
- temperatureThe reaction was cooled
- customThe organic layer was separated
- concentrationconcentrated in vacuo
- customThe crude product was purified by flash chromatography with a gradient from 0-30% ethyl acetate in hexanes
출처 및 근거
- ORD 기록
- ord-7ac90e32f2534afb8fb10579fcfc86d0
- 출처 데이터셋
- uspto-grants-2011_05
- 특허 번호
- US07947728B1
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