Potassium Carbonate → HCID 11430796, compound

HRID 130664Notes

Reaction equation

HRID 130664 reaction equation
[OH:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6]([O:12][C:13]3[CH:26]=[CH:25][C:16]4[C:17]([C:21]([NH:23][CH3:24])=[O:22])=[C:18]([CH3:20])[O:19][C:15]=4[CH:14]=3)=[CH:7][CH:8]=[N:9]2)=[CH:4][CH:3]=1.Br[CH2:28][CH:29]1[CH2:31]O1.[C:32]([O-:35])([O-:34])=[O:33].[K+].[K+]>CN(C=O)C>[CH3:24][NH:23][C:21]([C:17]1[C:16]2[CH:25]=[CH:26][C:13]([O:12][C:6]3[C:5]4[C:10](=[CH:11][C:2]([O:1][CH2:28][CH:29]5[CH2:31][O:34][C:32](=[O:35])[O:33]5)=[CH:3][CH:4]=4)[N:9]=[CH:8][CH:7]=3)=[CH:14][C:15]=2[O:19][C:18]=1[CH3:20])=[O:22]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 18430EpibromohydrinHCID 135507449HCID 135507449, compound

Product 1

HCID 11430796HCID 11430796, compoundYield 50.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 6-[(7-hydroxyquinolin-4-yl)oxy]-N,2-dimethyl-1-benzofuran-3-carboxamide 110-A13(500mg, 1.43 mmol), 2-(bromomethyl)oxirane (286mg, 2.1 mmol) and K2CO3 (386mg, 2.8 mmol) in DMF(15 mL) was stirred at 90° C. for 3h. The mixture was then extracted with EtOAc. The concentrated residue was purified by silica gel column chromatography using 0-5% MeOH/CH2Cl2 to give N,2-dimethyl-6-({7-[(2-oxo-1,3-dioxolan-4-yl)methoxy]quinolin-4-yl}oxy)-1-benzofuran-3-carboxamide 110 (323 mg).

Workup

  1. extractionThe mixture was then extracted with EtOAc
  2. customThe concentrated residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-391e1ff220274a6e848abf82494c4e0d
Source dataset
uspto-grants-2008_06
Patent number
US07381824B2

Reaction notes

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