Cesium carbonate → HCID 24822778, compound

HRID 1925363Notes

Reaction equation

HRID 1925363 reaction equation
[F:1][C:2]1[C:11]([OH:12])=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][CH:6]=[C:7]2[C:13]([OH:15])=[O:14].C([O-])([O-])=O.[Cs+].[Cs+].Cl[C:23]1[C:32]2[C:27](=[CH:28][C:29]([O:35][CH3:36])=[C:30]([O:33][CH3:34])[CH:31]=2)[N:26]=[CH:25][CH:24]=1>CS(C)=O>[CH3:34][O:33][C:30]1[CH:31]=[C:32]2[C:27](=[CH:28][C:29]=1[O:35][CH3:36])[N:26]=[CH:25][CH:24]=[C:23]2[O:12][C:11]1[C:2]([F:1])=[C:3]2[C:8](=[CH:9][CH:10]=1)[C:7]([C:13]([OH:15])=[O:14])=[CH:6][CH:5]=[CH:4]2

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 4596104-Chloro-6,7-dimethoxyquinolineHCID 248246045-Fluoro-6-hydroxynaphthalene-1-carboxylic acid

Product 1

HCID 24822778HCID 24822778, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

To a solution of 5-fluoro-6-hydroxy-1-naphthoic acid (1 g, 4.87 mmol) in DMSO (5 mL), Cs2CO3 (4.75 g, 14.61 mmol) was added in one portion. The mixture was stirred at RT 10 min. To the suspension, 4-chloro-6,7-dimethoxyquinoline (1.09 g, 4.87 mmol) was added and the mixture heated to 140° C. O/N. The mixture was allowed to cool to RT, pH adjusted to 7 and the resulting solid filtered and rinsed with water. The title compound was obtained as a tan solid.

Workup

  1. temperaturethe mixture heated to 140° C
  2. temperatureto cool to RT
  3. filtrationthe resulting solid filtered
  4. washrinsed with water

Sources & evidence

ORD record
ord-1cd174abc31e4697a268cfdd4bc1a4c5
Source dataset
uspto-grants-2012_05
Patent number
US08178557B2

Reaction notes

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