Benzophenone imine → HCID 86692536, compound

HRID 1748586Notes

Reaction equation

HRID 1748586 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH:12]=[C:11]([C:14]2[C:19]([CH3:20])=[CH:18][C:17](Br)=[CH:16][N:15]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(P(C(C)(C)C)C1C=CC2C(=CC=CC=2)C=1C1C2C(=CC=CC=2)C=CC=1)(C)(C)C.C(O[Na])(C)(C)C.C(=[NH:70])(C1C=CC=CC=1)C1C=CC=CC=1.O.NO.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.O.C(O)C>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH:12]=[C:11]([C:14]2[C:19]([CH3:20])=[CH:18][C:17]([NH2:70])=[CH:16][N:15]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

12

Reactant 7

HCID 136809Benzophenone imineHCID 516892Sodium BicarbonateHCID 517045Sodium AcetateHCID 2734941(1,1'-Binaphthalen)-2-yldi-tert-butylphosphineHCID 22235265HCID 22235265, compoundHCID 86692537HCID 86692537, compoundHCID 178418730sodium 2-methylpropan-2-olate

Product 1

HCID 86692536HCID 86692536, compound

Reagents, catalysts & solvents 4

HCID 167845palladium(II) acetateCatalystHCID 702EthanolSolventHCID 962WaterSolventHCID 1140TolueneSolvent

Conditions

Temperature
120 °C

Procedure

To a suspension of 4-(5-bromo-3-methylpyridin-2-yl)-1,2,3,6-tetrahydropyridine-1-carboxylic acid tert-butyl ester (4.83 g), palladium(II) acetate (384 mg), (±)-2-(di-tert-butylphosphino)-1,1′-binaphthyl (1.06 g), and tert-butoxysodium (1.97 g) in toluene (34 ml) was added benzophenone imine (2.29 ml), stirred at 120° C. for 3.5 hours, then ethanol (34 ml), water (34 ml), hydroxylamine monohydrate (4.0 g), and sodium acetate (6.73 g) were added thereto at room temperature, and stirred at room temperature for 4 hours. To the reaction solution was added a saturated aqueous solution of sodium hydrogen carbonate, extracted with ethyl acetate, washed with saturated brine, dried over anhydrous sodium sulfate, and then the solvent was evaporated in vacuo. The obtained residue was purified with basic silica gel chromatography (n-hexane/ethyl acetate) to give 4-(5-amino-3-methylpyridin-2-yl)-1,2,3,6-tetrahydropyridine-1-carboxylic acid tert-butyl ester (2.4 g) as a yellow oil.

Workup

  1. stirringat room temperature, and stirred at room temperature for 4 hours
  2. extractionextracted with ethyl acetate
  3. washwashed with saturated brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. customthe solvent was evaporated in vacuo
  6. customThe obtained residue was purified with basic silica gel chromatography (n-hexane/ethyl acetate)

Sources & evidence

ORD record
ord-d077b449293147c3ab3a8dd2f9307842
Source dataset
uspto-grants-2015_10
Patent number
US09150555B2

Reaction notes

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