Cesium carbonate → HCID 86712402, compound

HRID 2174197Notes

Reaction equation

HRID 2174197 reaction equation
Br[C:2]1[C:3]([C:8]([CH3:12])([CH3:11])[CH:9]=[O:10])=[N:4][CH:5]=[CH:6][CH:7]=1.[F:13][C:14]1[CH:15]=[CH:16][CH:17]=[C:18]2[C:23]=1[N:22]=[CH:21][C:20]([OH:24])=[CH:19]2.C(=O)([O-])[O-].[Cs+].[Cs+].C(CC(=O)C(C)(C)C)(=O)C(C)(C)C>CN1CCCC1=O.[Cu]Cl>[F:13][C:14]1[CH:15]=[CH:16][CH:17]=[C:18]2[C:23]=1[N:22]=[CH:21][C:20]([O:24][C:2]1[C:3]([C:8]([CH3:12])([CH3:11])[CH:9]=[O:10])=[N:4][CH:5]=[CH:6][CH:7]=1)=[CH:19]2

Participants

7

Reactant 4

HCID 10796Cesium carbonateHCID 707002,2,6,6-Tetramethyl-3,5-heptanedioneHCID 682880678-fluoroquinolin-3-olHCID 86712401HCID 86712401, compound

Product 1

HCID 86712402HCID 86712402, compoundYield 34.1%

Reagents, catalysts & solvents 2

HCID 62652Cuprous chlorideCatalystHCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
130 °C

Procedure

0.41 g of 2-(3-bromo-pyridin-2-yl)-2-methyl-propioaldehyde were dissolved in 4 ml of N-methylpyrrolidone. 0.59 g of 8-fluoro-3-hydroxyquinoline, 1.2 g of cesium carbonate, 0.07 g of dipivaloylmethane and 0.18 g of copper (I) chloride were added thereto followed by stirring for 16 hours at 130° C. Subsequently, the reaction solution was cooled to room temperature and purified by silica gel column chromatography to obtain 0.19 g of 2-[3-(8-fluoro-quinolin-3-yloxy)-pyridin-2-yl]-2-methyl-propioaldehyde.

Workup

  1. temperatureSubsequently, the reaction solution was cooled to room temperature
  2. custompurified by silica gel column chromatography

Sources & evidence

ORD record
ord-eadc2c79f80849ab90c59f73ca1314f0
Source dataset
uspto-grants-2015_06
Patent number
US09060517B2

Reaction notes

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