Water → HCID 86680797, compound

HRID 2402374Notes

Reaction equation

HRID 2402374 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][N:6]=[C:5]([NH2:9])[CH:4]=1.[Br:10][C:11]1[CH:16]=[C:15]([CH3:17])[CH:14]=[C:13](Br)[N:12]=1.CC(C)([O-])C.[Na+].O>O1CCOCC1.[Pd](Cl)Cl.C(P(C(C)(C)C)[C-]1C=CC=C1)(C)(C)C.[C-]1(P(C(C)(C)C)C(C)(C)C)C=CC=C1.[Fe+2]>[Br:10][C:11]1[N:12]=[C:13]([NH:9][C:5]2[CH:4]=[C:3]([O:2][CH3:1])[CH:8]=[CH:7][N:6]=2)[CH:14]=[C:15]([CH3:17])[CH:16]=1

Participants

7

Reactant 4

HCID 962WaterHCID 108987152-Amino-4-MethoxypyridineHCID 112881742,6-Dibromo-4-methylpyridineHCID 23676156Sodium t-butoxide

Product 1

HCID 86680797HCID 86680797, compoundYield 50%

Reagents, catalysts & solvents 2

HCID 178454861HCID 178454861, compoundCatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 4-methoxypyridin-2-amine (620 mg, 5 mmol) and 2,6-dibromo-4-methylpyridine (1123 mg, 5.25 mmol) in dioxane (18 mL) was added 1,1′-bis(di-tertbutylphosphino)ferrocene palladium dichloride (280 mg, 0.5 mmol) and sodium tert-butoxide (437 mg, 5.25 mmol). Then the mixture stirred under microwave irradiation for 1.5 hours at 80° C. Then the mixture was poured into water (50 mL), and extracted with EtOAc (100 mL). The organic layer was washed with water (50 mL) and brine (50 mL), dried and concentrated. The residue purified by silica gel chromatography using a solvent system of 75% petroleum ether/EtOAc. The product containing fractions were collected and concentrated to give 6-bromo-N-(4-methoxypyridin-2-yl)-4-methylpyridin-2-amine (627 mg, 50%). MS ESI calcd for C12H12BrN3O [M+H]+ 294, found 294.

Workup

  1. extractionextracted with EtOAc (100 mL)
  2. washThe organic layer was washed with water (50 mL) and brine (50 mL)
  3. customdried
  4. concentrationconcentrated
  5. customThe residue purified by silica gel chromatography
  6. additionThe product containing fractions
  7. customwere collected
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-5dec5d1a01694c98af1423ab20711dbd
Source dataset
uspto-grants-2014_08
Patent number
US08796310B2

Reaction notes

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