Potassium Carbonate → 6′-Methoxy[3,3′-bipyridin]-6-amine

HRID 626921Notes

Reaction equation

HRID 626921 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5](Br)=[CH:4][N:3]=1.[CH3:9][O:10][C:11]1[N:16]=[CH:15][C:14](B(O)O)=[CH:13][CH:12]=1.C(=O)([O-])[O-].[K+].[K+]>O1CCOCC1.C(OCC)C>[CH3:9][O:10][C:11]1[N:16]=[CH:15][C:14]([C:5]2[CH:6]=[CH:7][C:2]([NH2:1])=[N:3][CH:4]=2)=[CH:13][CH:12]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 706222-Amino-5-bromopyridineHCID 2734368(6-Methoxypyridin-3-yl)boronic acid

Product 1

HCID 624899756′-Methoxy[3,3′-bipyridin]-6-amineYield 83%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 312751,4-DioxaneSolvent

Procedure

A degassed mixture of 2-amino-5-bromopyridine (3.5 g, 20.23 mmol), 6-methoxypyridin-3-ylboronic acid (3.71 g, 24.28 mmol) and bis[3-(diphenylphosphanyl)-cyclopenta-2,4-dien-1-yl]iron-dichloropalladium-dichloromethane complex (413 mg, 0.51 mmol) in 1,4-dioxane (36 mL) and a 2M aqueous potassium carbonate solution (36.4 mL) was heated at 90° C. under a nitrogen atmosphere for approximately 16 h. The reaction mixture was allowed to cool to room temperature and diluted with diethyl ether (100 mL). The organic phase was separated off, washed with brine, dried over sodium sulfate and concentrated under vacuum. The crude product was triturated with DCM (10 mL) and filtered, to afford the title compound (3.36 g, 83%) as a light brown solid. Method C LCMS: MH+ m/z 202, RT 0.60 minutes.

Workup

  1. customThe organic phase was separated off
  2. washwashed with brine
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated under vacuum
  5. customThe crude product was triturated with DCM (10 mL)
  6. filtrationfiltered

Sources & evidence

ORD record
ord-6228cadfe96f4f6295c36eedbead8276
Source dataset
uspto-grants-2016_04
Patent number
US09309243B2

Reaction notes

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