Benzophenone imine → HCID 86692519, compound

HRID 1748574Notes

Reaction equation

HRID 1748574 reaction equation
[C:1]([O:5][C:6](=[O:23])[N:7]([CH:9]1[CH2:14][CH2:13][C:12]([C:15]2[C:20]([CH3:21])=[CH:19][C:18](Br)=[CH:17][N:16]=2)=[CH:11][CH2:10]1)[CH3:8])([CH3:4])([CH3:3])[CH3:2].C(=[NH:37])(C1C=CC=CC=1)C1C=CC=CC=1.CC(C)([O-])C.[Na+].Cl.ON.C([O-])(=O)C.[Na+].C(=O)([O-])O.[Na+]>C1(C)C=CC=CC=1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C1(P(C2C=CC=CC=2)C2C=CC3C(=CC=CC=3)C=2C2C3C(=CC=CC=3)C=CC=2P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[C:1]([O:5][C:6](=[O:23])[N:7]([CH:9]1[CH2:14][CH2:13][C:12]([C:15]2[C:20]([CH3:21])=[CH:19][C:18]([NH2:37])=[CH:17][N:16]=2)=[CH:11][CH2:10]1)[CH3:8])([CH3:4])([CH3:3])[CH3:2]

Participants

10

Reactant 6

HCID 136809Benzophenone imineHCID 443297Hydroxyamine hydrochlorideHCID 516892Sodium BicarbonateHCID 517045Sodium AcetateHCID 23676156Sodium t-butoxideHCID 86692517HCID 86692517, compound

Product 1

HCID 86692519HCID 86692519, compound

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 634876Binap, (A+-)-CatalystHCID 1140TolueneSolvent

Conditions

Temperature
120 °C

Procedure

To a solution of N-[4-(5-bromo-3-methylpyridin-2-yl)cyclohex-3-en-1-yl]-N-methylcarbamic acid-tert-butyl ester (1.25 g) in toluene (17 ml) were added palladium acetate (18 mg), benzophenone imine (0.6 ml), (±)-2,2′-bis(diphenylphosphino)-1,1′-binaphthyl (51 mg) and sodium tert-butoxide (473 mg) at room temperature, and stirred at 120° C. for 0.5 hours. Then, after the mixture was cooled to room temperature, hydroxyamine monohydrochloride (683 mg) and sodium acetate (1.6 g) were added thereto, and stirred at the same temperature for 4 hours. After completion of the reaction, a saturated aqueous solution of sodium hydrogen carbonate was added thereto, and extracted with 10% methanol/chloroform solution. The organic layer was dried over anhydrous sodium sulfate, and then the solvent was evaporated. The obtained residue was purified with basic silica gel column chromatography (n-hexane/ethyl acetate) to give the titled compound (987 mg) as a pale yellow solid.

Workup

  1. temperatureThen, after the mixture was cooled to room temperature
  2. stirringstirred at the same temperature for 4 hours
  3. customAfter completion of the reaction
  4. extractionextracted with 10% methanol/chloroform solution
  5. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  6. customthe solvent was evaporated
  7. customThe obtained residue was purified with basic silica gel column chromatography (n-hexane/ethyl acetate)

Sources & evidence

ORD record
ord-c162cdf3534744a7a6eb44af3f88617a
Source dataset
uspto-grants-2015_10
Patent number
US09150555B2

Reaction notes

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