Water → HCID 15887918, compound

HRID 1018531Notes

Reaction equation

HRID 1018531 reaction equation
[CH3:1][C:2]([CH3:25])([CH3:24])[C:3]([N:5]1[CH2:13][C:12]2[C:7](=[CH:8][CH:9]=[C:10](B3OC(C)(C)C(C)(C)O3)[CH:11]=2)[C@H:6]1[CH3:23])=[O:4].Br[C:27]1[C:36]([O:37][CH:38]([F:40])[F:39])=[C:35]2[C:30]([C:31](=[O:49])[C:32]([C:44]([O:46][CH2:47][CH3:48])=[O:45])=[CH:33][N:34]2[CH:41]2[CH2:43][CH2:42]2)=[CH:29][CH:28]=1.C(=O)([O-])[O-].[Na+].[Na+].O>C(O)C.[Pd].CC(C)=O>[CH:41]1([N:34]2[C:35]3[C:30](=[CH:29][CH:28]=[C:27]([C:10]4[CH:11]=[C:12]5[C:7](=[CH:8][CH:9]=4)[C@@H:6]([CH3:23])[N:5]([C:3](=[O:4])[C:2]([CH3:1])([CH3:24])[CH3:25])[CH2:13]5)[C:36]=3[O:37][CH:38]([F:40])[F:39])[C:31](=[O:49])[C:32]([C:44]([O:46][CH2:47][CH3:48])=[O:45])=[CH:33]2)[CH2:42][CH2:43]1

Participants

8

Reactant 4

HCID 962WaterHCID 10340Sodium CarbonateHCID 11732152Ethyl 7-bromo-1-cyclopropyl-8-(difluoromethoxy)-4-oxo-1,4-dihydroquinoline-3-carboxylateHCID 54392773HCID 54392773, compound

Product 1

HCID 15887918HCID 15887918, compoundYield 96%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 180AcetoneSolventHCID 702EthanolSolvent

Procedure

In 15 ml of ethanol is dissolved 2.5 g of (R)-2-(2,2-dimethylpropanoyl)-1-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)isoindoline, and thereto are added 2.8 g of ethyl 7-bromo-1-cyclopropyl-8-difluoromethoxy-1,4-dihydro-4-oxoquinoline-3-carboxylate and 1.1 g of sodium carbonate. Subsequently, 150 mg of 10% palladium-activated carbon is added to the mixture in a nitrogen atmosphere and thereafter the resulting mixture is heated under reflux for 3 hours in the same atmosphere. The reaction mixture is cooled and thereafter added to a mixed solvent of 15 ml of water and 30 ml of acetone, and the crystals deposited are collected by filtration to obtain 3.6 g of ethyl (R)-1-cyclopropyl-8-difluoromethoxy-7-[2-(2,2-dimethylpropanoyl)-1-methyl-2,3-dihydro-1H-5-isoindolyl]-4-oxo-1,4-dihydro-3-quinolinecarboxylate.

Workup

  1. temperaturethe resulting mixture is heated
  2. temperatureunder reflux for 3 hours in the same atmosphere
  3. temperatureThe reaction mixture is cooled
  4. filtrationthe crystals deposited are collected by filtration

Sources & evidence

ORD record
ord-d212b60c8737465aa76093b5e38df7f7
Source dataset
uspto-grants-2002_11
Patent number
US06482835B2

Reaction notes

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