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Cesium carbonate → Tert-butyl 3-(5-bromo-4-fluoro-2-(6-(N-(isoxazol-3-yl)-N-(4-methoxybenzyl)sulfamoyl)-2-oxoquinolin-1(2H)-yl)phenoxy)pyrrolidine-1-carboxylate

HRID 1504377
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HRID 1504377 반응식
I[CH:2]1[CH2:6][CH2:5][N:4]([C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])[CH2:3]1.[Br:14][C:15]1[C:20]([F:21])=[CH:19][C:18]([N:22]2[C:31]3[C:26](=[CH:27][C:28]([S:32]([N:35]([C:45]4[CH:49]=[CH:48][O:47][N:46]=4)[CH2:36][C:37]4[CH:42]=[CH:41][C:40]([O:43][CH3:44])=[CH:39][CH:38]=4)(=[O:34])=[O:33])=[CH:29][CH:30]=3)[CH:25]=[CH:24][C:23]2=[O:50])=[C:17]([OH:51])[CH:16]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>C(#N)C>[Br:14][C:15]1[C:20]([F:21])=[CH:19][C:18]([N:22]2[C:31]3[C:26](=[CH:27][C:28]([S:32](=[O:33])(=[O:34])[N:35]([C:45]4[CH:49]=[CH:48][O:47][N:46]=4)[CH2:36][C:37]4[CH:38]=[CH:39][C:40]([O:43][CH3:44])=[CH:41][CH:42]=4)=[CH:29][CH:30]=3)[CH:25]=[CH:24][C:23]2=[O:50])=[C:17]([CH:16]=1)[O:51][CH:2]1[CH2:6][CH2:5][N:4]([C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])[CH2:3]1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

5

반응물 3

HCID 10796Cesium carbonateHCID 23251108tert-Butyl 3-iodopyrrolidine-1-carboxylateHCID 1177372691-(4-bromo-5-fluoro-2-hydroxyphenyl)-N-(isoxazol-3-yl)-N-(4-methoxybenzyl)-2-oxo-1,2-dihydroquinoline-6-sulfonamide

생성물 1

HCID 117737147Tert-butyl 3-(5-bromo-4-fluoro-2-(6-(N-(isoxazol-3-yl)-N-(4-methoxybenzyl)sulfamoyl)-2-oxoquinolin-1(2H)-yl)phenoxy)pyrrolidine-1-carboxylate

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

Tert-butyl 3-iodopyrrolidine-1-carboxylate (0.029 g, 0.097 mmol) was added to a solution of 1-(4-bromo-5-fluoro-2-hydroxyphenyl)-N-(isoxazol-3-yl)-N-(4-methoxybenzyl)-2-oxo-1,2-dihydroquinoline-6-sulfonamide (0.058 g, 0.097 mmol) and cesium carbonate (0.063 g, 0.193 mmol) in acetonitrile (0.242 ml) and stirred for 48 hr. The reaction vessel was cooled to room temperature. The reaction mixture was then transferred to a sep. funnel and the aqueous layer was washed 3× with EtOAc. The organic layers were combined, dried with MgSO4, filtered and concentrated to an oil. The crude mixture was taken onward to the next step assuming quantitative yield. m/z (ESI) 670.9 (M+H)+.

후처리

  1. washfunnel and the aqueous layer was washed 3× with EtOAc
  2. dry with materialdried with MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated to an oil

출처 및 근거

ORD 기록
ord-3bd6034c5a5e47f38870889303cbf3ec
출처 데이터셋
uspto-grants-2015_12
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09212182B2

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