2-Bromopyridine → HCID 66627785, compound

HRID 1970744Notes

Reaction equation

HRID 1970744 reaction equation
[CH3:1][C:2]1[N:7]=[C:6]([NH:8][C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([CH3:15])[N:10]=2)[CH:5]=[CH:4][CH:3]=1.Br[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][N:18]=1.C(=O)([O-])[O-].[Na+].[Na+].[Br-].[K+]>[Cu].O>[CH3:1][C:2]1[N:7]=[C:6]([N:8]([C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([CH3:15])[N:10]=2)[C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][N:18]=2)[CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 79732-BromopyridineHCID 10340Sodium CarbonateHCID 253877Potassium BromideHCID 30210056-Methyl-N-(6-methyl-2-pyridyl)pyridin-2-amine

Product 1

HCID 66627785HCID 66627785, compound

Reagents, catalysts & solvents 2

HCID 23978CopperCatalystHCID 962WaterSolvent

Procedure

To a flask were added 2.0 g of 6-methyl-N-(6-methylpyridin-2-yl)pyridin-2-amine, 4.7 g of 2-bromopyridine, 1.6 g of sodium carbonate, 51 mg of copper bronze, 5 mg of potassium bromide, and 3 ml of mesytylene. After stirring under nitrogen at 160 C for 16 hours, the mixture was cooled to 22 C, and 35 ml of water was added and the product was extracted with 50 ml ethyl acetate. After washing twice with 20 ml of water, the solvent was removed, and the product was purified by silica gel chromatography using 60% ethyl acetate, 40% hexane, and 0.1% triethylamine resulting in 2.2 g of a yellow oil.

Workup

  1. additionwas added
  2. extractionthe product was extracted with 50 ml ethyl acetate
  3. washAfter washing twice with 20 ml of water
  4. customthe solvent was removed
  5. customthe product was purified by silica gel chromatography

Sources & evidence

ORD record
ord-fc958eb361274cbca61280306acca33f
Source dataset
uspto-grants-2013_04
Patent number
US08431045B2

Reaction notes

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