2,5-Dibromopyridine → HCID 57556030, compound

HRID 658084Notes

Reaction equation

HRID 658084 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([Br:8])=[CH:4][N:3]=1.[F:9][C:10]([F:24])([F:23])[C:11]1[CH:12]=[C:13]([CH:16]=[C:17]([C:19]([F:22])([F:21])[F:20])[CH:18]=1)[CH2:14][NH2:15].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.CC(C)([O-])C.[Na+].C(=O)(O)[O-].[Na+]>C1(C)C=CC=CC=1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[F:9][C:10]([F:23])([F:24])[C:11]1[CH:12]=[C:13]([CH:16]=[C:17]([C:19]([F:22])([F:20])[F:21])[CH:18]=1)[CH2:14][NH:15][C:2]1[CH:7]=[CH:6][C:5]([Br:8])=[CH:4][N:3]=1

Participants

8

Reactant 5

HCID 693532,5-DibromopyridineHCID 516892Sodium BicarbonateHCID 5210993,5-Bis(trifluoromethyl)benzylamineHCID 634876Binap, (A+-)-HCID 23676156Sodium t-butoxide

Product 1

HCID 57556030HCID 57556030, compoundYield 26%

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 1140TolueneSolvent

Conditions

Temperature
80 °C

Procedure

2,5-Dibromopyridine (4.74 g) is dissolved in toluene (100 ml) and thereto are added 3,5-bis-trifluoromethyl-benzylamine (5.84 g) and palladium acetate (449.0 mg), 2,2′-bis(diphenylphosphino)-1,1′-binaphthyl (1.25 g) and sodium tert-butoxide (4.23 g) and the mixture is stirred under nitrogen atmosphere at 80° C. for 12 hours. The reaction solution is cooled to room temperature, and thereto is added a saturated aqueous sodium bicarbonate solution and the mixture is extracted with ethyl acetate twice, and the organic layer is washed successively with water and a saturated brine, dried over magnesium sulfate, and concentrated under reduced pressure. The resulting residue is purified by silica gel column chromatography (hexane:ethyl acetate=19:1→4:1) to give (3,5-bis-trifluoromethyl-benzyl)-(5-bromopyridin-2-yl)-amine (2.08 g). MS (m/z): 399/401 [M+H]+

Workup

  1. temperatureThe reaction solution is cooled to room temperature
  2. extractionthe mixture is extracted with ethyl acetate twice
  3. washthe organic layer is washed successively with water
  4. dry with materiala saturated brine, dried over magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe resulting residue is purified by silica gel column chromatography (hexane:ethyl acetate=19:1→4:1)

Sources & evidence

ORD record
ord-98549381fed046dc9adcb9dcb7ee41ab
Source dataset
uspto-grants-2011_12
Patent number
US08076364B2

Reaction notes

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