Benzylamine → HCID 17985541, compound

HRID 910124Notes

Reaction equation

HRID 910124 reaction equation
Cl[C:2]1[CH:7]=[CH:6][C:5]([CH:8]([CH3:10])[CH3:9])=[CH:4][N:3]=1.[CH2:11]([NH2:18])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.CC(C)([O-])C.[Na+]>C1(C)C=CC=CC=1.CC([O-])=O.CC([O-])=O.[Pd+2].C1(C2C=CC=CC=2)C=CC=CC=1P(C1CCCCC1)C1CCCCC1>[CH2:11]([N:18]1[CH:4]=[C:5]([CH:8]([CH3:10])[CH3:9])[CH:6]=[CH:7][CH:2]1[NH2:3])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

7

Reactant 3

HCID 7504BenzylamineHCID 108665752-Chloro-5-(1-methylethyl)pyridineHCID 23676156Sodium t-butoxide

Product 1

HCID 17985541HCID 17985541, compoundYield 37,637%

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 27342162-(Dicyclohexylphosphino)biphenylCatalystHCID 1140TolueneSolvent

Conditions

Temperature
100 °C

Procedure

Dissolve 2-chloro-5-isopropylpyridine (5 g, 0.032 mol), benzylamine (6.8 g, 0.064 mmol), Biphenyl-2-yl-dicyclohexyl-phosphine (0.46 g, 1.3 mmol), Pd(OAc)2 (0.14 g, 0.64 mmol), and sodium tert-butoxide (4.3 g, 0.045 mol) in 60 mL of toluene. Deoxygenate three times. Heat at 100° C. for 18 hours. Cool and concentrate under reduced pressure. Subject the residue to silica gel chromatography, eluting with 1:1 hexanes:ethyl acetate to provide 5.5 g of the desired compound.

Workup

  1. customDeoxygenate three times
  2. temperatureCool
  3. concentrationconcentrate under reduced pressure
  4. washeluting with 1:1 hexanes

Sources & evidence

ORD record
ord-90035964792a4fbd8e34e4d45ac9d333
Source dataset
uspto-grants-2011_09
Patent number
US08022065B2

Reaction notes

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