2-Pyridinamine, 5-bromo-6-methyl- → 5-(4-Methoxyphenyl)-6-methylpyridin-2-amine

HRID 2093172Notes

Reaction equation

HRID 2093172 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6](B(O)O)=[CH:5][CH:4]=1.Br[C:13]1[CH:14]=[CH:15][C:16]([NH2:20])=[N:17][C:18]=1[CH3:19].C([O-])(=O)C.[K+]>ClCCl.[Pd](Cl)Cl.C1(P(C2C=CC=CC=2)[C-]2C=CC=C2)C=CC=CC=1.[C-]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C1.[Fe+2].O1CCOCC1>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:13]2[CH:14]=[CH:15][C:16]([NH2:20])=[N:17][C:18]=2[CH3:19])=[CH:5][CH:4]=1

Participants

6

Reactant 3

HCID 1706782-Pyridinamine, 5-bromo-6-methyl-HCID 201262(4-Methoxyphenyl)boronic acidHCID 517044Potassium Acetate

Product 1

HCID 577048485-(4-Methoxyphenyl)-6-methylpyridin-2-amine

Reagents, catalysts & solvents 2

HCID 178418807HCID 178418807, compoundCatalystHCID 312751,4-DioxaneSolvent

Procedure

(4-methoxyphenyl)boronic acid (1 g, 6.58 mmol), 5-bromo-6-methylpyridin-2-amine (1.23 g, 6.58 mmol), 1,1′-bis(diphenylphosphino)ferrocene-palladium dichloride dichloromethane adduct (537 mg, 0.658 mmol), potassium acetate (1.29 g, 13.16 mmol) and 1,4-dioxane (5 mL) were placed in a sealed tube and the mixture was subjected to microwave irradiation at 140° C. for 30 minutes. The resulting crude mixture was purified by flash column chromatography on SiO2 (Biotage 40+M cartridge, ethyl acetate) to afford 5-(4-methoxyphenyl)-6-methylpyridin-2-amine as a purple solid. LCMS calc.=214.11; found=215.17 (M+1)+.

Workup

  1. customirradiation at 140° C. for 30 minutes
  2. customThe resulting crude mixture was purified by flash column chromatography on SiO2 (Biotage 40+M cartridge, ethyl acetate)

Sources & evidence

ORD record
ord-8c39a40771854fe699965600b03621af
Source dataset
uspto-grants-2013_05
Patent number
US08440702B2

Reaction notes

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