Potassium Carbonate → HCID 58668623, compound

HRID 2054468Notes

Reaction equation

HRID 2054468 reaction equation
[NH2:1][C:2]1[N:9]=[CH:8][C:7](Br)=[CH:6][C:3]=1[CH:4]=[O:5].[CH3:11][O:12][C:13]1[CH:18]=[CH:17][C:16](B(O)O)=[CH:15][CH:14]=1.C(=O)([O-])[O-].[K+].[K+]>CC#N.O>[NH2:1][C:2]1[N:9]=[CH:8][C:7]([C:16]2[CH:17]=[CH:18][C:13]([O:12][CH3:11])=[CH:14][CH:15]=2)=[CH:6][C:3]=1[CH:4]=[O:5]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 201262(4-Methoxyphenyl)boronic acidHCID 242137922-Amino-5-bromo-3-pyridinecarbaldehyde

Product 1

HCID 58668623HCID 58668623, compoundYield 47%

Reagents, catalysts & solvents 1

HCID 18373917Acetonitrile--water (1/1)Solvent

Procedure

2-amino-5-bromonicotinaldehyde (1.61 g, 8 mmol), 4-methoxyphenylboronic acid (2.43 g, 16 mmol) and anhydrous potassium carbonate (2.21 g, 16 mmol) were dissolved in 50 ml of CH3CN/H2O (8:2), and 1 mol % of dichlorobis(triphenylphopsine)palladium(II) (56 mg, 0.08 mmol) was added while stirring. The reaction mixture was heated to reflux and stirred for 2 h. The reaction mixture was allowed to cool, and then partitioned between diethyl ether and water. The aqueous layer was extracted with another portion of diethyl ether. The combined organics were washed with brine, dried over anhydrous Na2SO4, filtered and concentrated in vacuo. The compound was purified by chromatography on silica gel eluting with with 30% EtOAc/hexanes to yield 2-amino-5-(4-methoxyphenyl)nicotinaldehyde (0.85 g, 47%).

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux
  3. stirringstirred for 2 h
  4. temperatureto cool
  5. custompartitioned between diethyl ether and water
  6. extractionThe aqueous layer was extracted with another portion of diethyl ether
  7. washThe combined organics were washed with brine
  8. dry with materialdried over anhydrous Na2SO4
  9. filtrationfiltered
  10. concentrationconcentrated in vacuo
  11. customThe compound was purified by chromatography on silica gel eluting with with 30% EtOAc/hexanes

Sources & evidence

ORD record
ord-e2ee435b509c401790749c10c3ed01a5
Source dataset
uspto-grants-2008_02
Patent number
US07329678B2

Reaction notes

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