Sodium Carbonate → 2-Methoxy-[3,4'-bipyridin]-2'-amine

HRID 250123

Reaction equation

HRID 250123 reaction equation
Br[C:2]1[CH:7]=[CH:6][N:5]=[C:4]([NH2:8])[CH:3]=1.[CH3:9][O:10][C:11]1[C:16](B(O)O)=[CH:15][CH:14]=[CH:13][N:12]=1.C(=O)([O-])[O-].[Na+].[Na+]>CN(C=O)C>[CH3:9][O:10][C:11]1[C:16]([C:2]2[CH:7]=[CH:6][N:5]=[C:4]([NH2:8])[CH:3]=2)=[CH:15][CH:14]=[CH:13][N:12]=1

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 6932822-Amino-4-bromopyridineHCID 2762709(2-Methoxypyridin-3-yl)boronic acid

Product 1

HCID 509572862-Methoxy-[3,4'-bipyridin]-2'-amineYield 93.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
85 °C

Procedure

To 4-bromopyridin-2-amine (0.5 g, 2.8 mmol), 2-methoxypyridin-3-ylboronic acid (0.52 g, 3.4 mmol) in DMF (25 mL) was added 1N sodium carbonate (10 mL, 2.3 mmol), followed by 1,1′-bis(diphenylphosphino)ferrocene-palladium(II)dichloride dichloromethane complex (0.21 g, 0.26 mmol). The reaction mixture was stirred for 3 hours at 85° C. and then cooled to room temperature. The product was extracted with ethyl acetate (2×50 mL), dried with MgSO4, filtered, and concentrated in vacuo. The crude product was purified by chromotography (Biotage: 100 to 90/10% ethyl acetate-ethyl acetate/methanol) to yield 2-methoxy-3,4′-bipyridin-2′-amine (0.53 g, 2.63 mmol, 93% yield) as a brown powder. The product was taken directly to the next step.

Workup

  1. temperaturecooled to room temperature
  2. extractionThe product was extracted with ethyl acetate (2×50 mL)
  3. dry with materialdried with MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe crude product was purified by chromotography (Biotage: 100 to 90/10% ethyl acetate-ethyl acetate/methanol)

Sources & evidence

ORD record
ord-a3e2247148e14db7a13681de1b3ce2c7
Source dataset
uspto-grants-2011_01
Patent number
US07863291B2

Linked notes

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