2-Bromopyridine → 6-Methyl-N-2-pyridinyl-2-pyridinemethanamine

HRID 495272Notes

Reaction equation

HRID 495272 reaction equation
C[C:2]1[N:7]=[C:6]([NH:8][C:9]2C=CC=CN=2)[CH:5]=[CH:4][CH:3]=1.Br[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][N:17]=1.[C:22](=O)([O-])[O-].[Na+].[Na+].[Br-].[K+]>[Cu].O>[CH3:22][C:18]1[N:17]=[C:16]([CH2:9][NH:8][C:6]2[CH:5]=[CH:4][CH:3]=[CH:2][N:7]=2)[CH:21]=[CH:20][CH:19]=1

Participants

7

Reactant 4

HCID 79732-BromopyridineHCID 10340Sodium CarbonateHCID 253877Potassium BromideHCID 15554650HCID 15554650, compound

Product 1

HCID 120323576-Methyl-N-2-pyridinyl-2-pyridinemethanamine

Reagents, catalysts & solvents 2

HCID 23978CopperCatalystHCID 962WaterSolvent

Procedure

To a flask were added 3.7 g of 6-methyl-N-pyridin-2-ylpyridin-2-amine, 9.4 g of 2-bromopyridine, 2.0 g of sodium carbonate, 0.05 g of copper bronze, 0.01 g of potassium bromide, and 5 ml of mesytylene. After stirring under nitrogen at 160 C for 10 hours, the mixture was cooled to 22 C, and 35 ml of water was added and the product was extracted with 75 ml ethyl acetate. After washing twice with 30 ml of water, the solvent was removed, and the product was purified by silica gel chromatography using 75% ethyl acetate, 25% hexane, and 0.01% triethylamine resulting in 3.2 g of a yellow oil.

Workup

  1. additionwas added
  2. extractionthe product was extracted with 75 ml ethyl acetate
  3. washAfter washing twice with 30 ml of water
  4. customthe solvent was removed
  5. customthe product was purified by silica gel chromatography

Sources & evidence

ORD record
ord-15395f28816841a59b31f5374263d281
Source dataset
uspto-grants-2009_05
Patent number
US07538931B2

Reaction notes

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