Cesium carbonate → HCID 68796911, compound

HRID 1375385Notes

Reaction equation

HRID 1375385 reaction equation
Br[C:2]1[CH:27]=[CH:26][C:5]([C:6]([N:8]2[C:14]3[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=3/[C:12](=[CH:19]/[C:20](OC)=[O:21])/[C:11]([F:25])([F:24])[CH2:10][CH2:9]2)=[O:7])=[C:4]([CH3:28])[CH:3]=1.[NH:29]([C:31]([O:33][C:34]([CH3:37])([CH3:36])[CH3:35])=[O:32])[NH2:30].[C:38](=O)([O-])[O-].[Cs+].[Cs+]>C1(C)C=CC=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[F:24][C:11]1([F:25])[CH2:10][CH2:9][N:8]([C:6]([C:5]2[CH:26]=[CH:27][C:2]([N:29]([C:31]([O:33][C:34]([CH3:37])([CH3:36])[CH3:35])=[O:32])[NH2:30])=[CH:3][C:4]=2[CH3:28])=[O:7])[C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=2/[C:12]/1=[CH:19]/[C:20]([CH3:38])=[O:21]

Participants

6

Reactant 3

HCID 10796Cesium carbonateHCID 70091tert-Butyl carbazateHCID 131726218HCID 131726218, compound

Product 1

HCID 68796911HCID 68796911, compoundYield 46.9%

Reagents, catalysts & solvents 2

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 1140TolueneSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of 2.0 g of the compound of Example 2 in 30 ml of toluene, 22.35 g of tert-butyl hydrazine carboxylate, 1.43 g of cesium carbonate, 400 mg of tris(dibenzylideneacetone)dipalladium (0), and 740 mg of 1,1′-bis(diphenylphosphine)ferrocene were added, and the mixture was stirred at 100° C. for 4 hours. After cooling the reaction solution, insoluble matter was filtered, and EtOAc and 10% citric acid aqueous solution were added to the filtrate to extract it. The organic layer was washed with water and brine, and dried over anhydrous sodium sulfate anhydride. After evaporation of the solvent, the residue was purified by silica gel column chromatography (hexane-EtOAc (2:1)) to obtain 1.0 g of tert-butyl 1-(4-{[(5Z)-4,4-difluoro-5-(2-methyl-2-oxoethylidene)-2,3,4,5-tetrahydro-1H-1-benzazepin-1-yl]carbonyl}-3-methylphenyl)hydrazine carboxylate.

Workup

  1. temperatureAfter cooling the reaction solution, insoluble matter
  2. filtrationwas filtered
  3. additionEtOAc and 10% citric acid aqueous solution were added to the filtrate
  4. extractionto extract it
  5. washThe organic layer was washed with water and brine
  6. dry with materialdried over anhydrous sodium sulfate anhydride
  7. customAfter evaporation of the solvent
  8. customthe residue was purified by silica gel column chromatography (hexane-EtOAc (2:1))

Sources & evidence

ORD record
ord-aa1a763538134d88b277a81f756a69e9
Source dataset
uspto-grants-2007_01
Patent number
US07169772B2

Reaction notes

Loading…