Hydrochloric Acid → 5-(6,7-Dimethoxyquinolin-4-yloxy)benzofuran-2-carboxylic acid

HRID 1865211Notes

Reaction equation

HRID 1865211 reaction equation
[OH:1][C:2]1[CH:3]=[CH:4][C:5]2[O:9][C:8]([C:10]([OH:12])=[O:11])=[CH:7][C:6]=2[CH:13]=1.C(=O)([O-])[O-].[Cs+].[Cs+].Cl[C:21]1[C:30]2[C:25](=[CH:26][C:27]([O:33][CH3:34])=[C:28]([O:31][CH3:32])[CH:29]=2)[N:24]=[CH:23][CH:22]=1.Cl>CS(C)=O.O>[CH3:32][O:31][C:28]1[CH:29]=[C:30]2[C:25](=[CH:26][C:27]=1[O:33][CH3:34])[N:24]=[CH:23][CH:22]=[C:21]2[O:1][C:2]1[CH:3]=[CH:4][C:5]2[O:9][C:8]([C:10]([OH:12])=[O:11])=[CH:7][C:6]=2[CH:13]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 10796Cesium carbonateHCID 4596104-Chloro-6,7-dimethoxyquinolineHCID 122089725-Hydroxybenzofuran-2-carboxylic acid

Product 1

HCID 579760675-(6,7-Dimethoxyquinolin-4-yloxy)benzofuran-2-carboxylic acid

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Procedure

To a stirred solution of 5-hydroxybenzofuran-2-carboxylic acid (Step a, 2.00 g, 11.23 mmol) in DMSO (23 mL) at RT was added cesium carbonate (11.0 g, 33.7 mmol). The reaction was stirred for 10 min followed by the addition of 4-chloro-6,7-dimethoxyquinoline (prepared by the method described in WO 03/33472) (1.75 g, 7.86 mmol). The reaction was stirred at 100° C. for 16 h. After cooling to RT, water was added. The aqueous layer was acidified with a 6M aqueous hydrochloric acid solution until pH=5, filtered and the solid was suspended in EtOAc. The organic phase was extracted with a 3M sodium hydroxide aqueous solution. After acidification of the aqueous layer, the title compound was isolated by filtration and dried under high vacuum.

Workup

  1. customprepared by the method
  2. stirringThe reaction was stirred at 100° C. for 16 h
  3. filtrationfiltered
  4. extractionThe organic phase was extracted with a 3M sodium hydroxide aqueous solution

Sources & evidence

ORD record
ord-5da38e8e3ae8414a9808a1b21bc91e34
Source dataset
uspto-grants-2009_12
Patent number
US07626030B2

Reaction notes

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