Cesium carbonate → HCID 68288080, compound

HRID 1618904Notes

Reaction equation

HRID 1618904 reaction equation
[F:1][C:2]1[C:11]([F:12])=[C:10]2[C:5]([CH:6]=[C:7](I)[CH:8]=[N:9]2)=[CH:4][CH:3]=1.[F:14][C:15]1[CH:20]=[CH:19][CH:18]=[C:17]([OH:21])[C:16]=1[C:22]([CH3:27])([CH3:26])[C:23](=[O:25])[CH3:24].C(=O)([O-])[O-].[Cs+].[Cs+].C(CC(=O)C(C)(C)C)(=O)C(C)(C)C>[Cu]Cl.CN1CCCC1=O>[F:1][C:2]1[C:11]([F:12])=[C:10]2[C:5]([CH:6]=[C:7]([O:21][C:17]3[CH:18]=[CH:19][CH:20]=[C:15]([F:14])[C:16]=3[C:22]([CH3:27])([CH3:26])[C:23](=[O:25])[CH3:24])[CH:8]=[N:9]2)=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 10796Cesium carbonateHCID 707002,2,6,6-Tetramethyl-3,5-heptanedioneHCID 68285982HCID 68285982, compoundHCID 86673628HCID 86673628, compound

Product 1

HCID 68288080HCID 68288080, compoundYield 10.5%

Reagents, catalysts & solvents 2

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

Conditions

Temperature
130 °C

Procedure

3 ml of N-methylpyrrolidone was added to 0.78 g of 7,8-difluoro-3-iodoquinoline, 0.26 g of 3-(2-fluoro-6-hydroxyphenyl)-3-methyl-butan-2-one, 1.05 g of cesium carbonate, 53 mg of dipivaloylmethane, and 0.27 g of copper (I) chloride. After 48 hours of stirring at 130° C., the reaction solution was filtered with CELITE and the liquid was separated with ethyl acetate. The organic layer was concentrated and purified by silica gel column chromatography to obtain 0.05 g of 3-[2-(7,8-difluoroquinolin-3-yloxy)-6-fluoro-phenyl]-3-methyl-butan-2-one (Compound Number 267).

Workup

  1. filtrationthe reaction solution was filtered with CELITE
  2. customthe liquid was separated with ethyl acetate
  3. concentrationThe organic layer was concentrated
  4. custompurified by silica gel column chromatography

Sources & evidence

ORD record
ord-3e621e29b1e64254a01172892f968870
Source dataset
uspto-grants-2014_07
Patent number
US08772200B2

Reaction notes

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