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 1504377Notes

Reaction equation

HRID 1504377 reaction equation
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

Participants

5

Reactant 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

Product 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

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

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)+.

Workup

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

Sources & evidence

ORD record
ord-3bd6034c5a5e47f38870889303cbf3ec
Source dataset
uspto-grants-2015_12
Patent number
US09212182B2

Reaction notes

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