2-Bromopyridine → 2-methyl-N-(6-methylpyridin-2-yl)-N-pyridin-2-ylquinolin-8-amine

HRID 1471289Notes

Reaction equation

HRID 1471289 reaction equation
[CH3:1][C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[C:5]([NH:12][C:13]3[CH:18]=[CH:17][CH:16]=[C:15]([CH3:19])[N:14]=3)[CH:6]=[CH:7][CH:8]=2)[N:3]=1.Br[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][N:22]=1.C(=O)([O-])[O-].[Na+].[Na+].[Br-].[K+]>[Cu].O>[CH3:1][C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[C:5]([N:12]([C:13]3[CH:18]=[CH:17][CH:16]=[C:15]([CH3:19])[N:14]=3)[C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][N:22]=3)[CH:6]=[CH:7][CH:8]=2)[N:3]=1

Participants

7

Reactant 4

HCID 79732-BromopyridineHCID 10340Sodium CarbonateHCID 253877Potassium BromideHCID 666278362-methyl-N-(6-methylpyridin-2-yl)quinolin-8-amine

Product 1

HCID 666279862-methyl-N-(6-methylpyridin-2-yl)-N-pyridin-2-ylquinolin-8-amine

Reagents, catalysts & solvents 2

HCID 23978CopperCatalystHCID 962WaterSolvent

Procedure

To a flask were added 2.5 g of 2-methyl-N-(6-methylpyridin-2-yl)quinolin-8-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 50% ethyl acetate, 50% hexane, and 0.1% triethylamine resulting in 3.0 g of a light 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-841d9c75191c40d9aa31fb3ff8c13f7d
Source dataset
uspto-grants-2015_04
Patent number
US09011734B2

Reaction notes

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