3-Pyridinylboronic acid → HCID 57813735, compound

HRID 447019

Reaction equation

HRID 447019 reaction equation
Br[C:2]1[CH:8]=[C:7]([N+:9]([O-:11])=[O:10])[C:5]([NH2:6])=[C:4]([N+:12]([O-:14])=[O:13])[CH:3]=1.[N:15]1[CH:20]=[CH:19][CH:18]=[C:17](B(O)O)[CH:16]=1>COCCOC.C(=O)([O-])O.[Na+]>[N+:9]([C:7]1[CH:8]=[C:2]([C:17]2[CH:16]=[N:15][CH:20]=[CH:19][CH:18]=2)[CH:3]=[C:4]([N+:12]([O-:14])=[O:13])[C:5]=1[NH2:6])([O-:11])=[O:10]

Participants

5

Reactant 2

HCID 27343783-Pyridinylboronic acidHCID 37466084-Bromo-2,6-dinitroaniline

Product 1

HCID 57813735HCID 57813735, compound

Reagents, catalysts & solvents 2

HCID 80711,2-DimethoxyethaneSolventHCID 516892Sodium BicarbonateSolvent2×

Procedure

A stirred solution of 4-Bromo-2,6-dinitroaniline (3 g, 11.45 mmol) in 1,2-dimethoxyethane (83 ml) was purged with nitrogen for 15 min and treated with aqueous sodium hydrogen carbonate solution (1M, 22.8 ml) followed by pyridine 3-boronic acid (2.1 g, 17.17 mmol) and 1,1-bis-(diphenylphosphino)ferrocene palladium (II) chloride complex (0.94 g, 1.15 mmol). The resultant mixture was boiled under reflux in a nitrogen atmosphere for 18 h. After cooling to ambient temperature, the dark mixture was diluted with saturated aqueous sodium hydrogen carbonate solution (300 ml) and extracted with ethyl acetate (3×250 ml). This was dried (MgSO4) and the solvent removed in vacuo to give a residue which was purified by flash chromatography (silica) eluting with 30% to 100% ethyl acetate in 40-60 petroleum ether. The 2,6-Dinitro-4-pyridin-3-yl-aniline was obtained as a yellow solid (1.46 g, 49%).

Workup

  1. temperatureunder reflux in a nitrogen atmosphere for 18 h
  2. extractionextracted with ethyl acetate (3×250 ml)
  3. dry with materialThis was dried (MgSO4)
  4. customthe solvent removed in vacuo
  5. customto give a residue which
  6. customwas purified by flash chromatography (silica)
  7. washeluting with 30% to 100% ethyl acetate in 40-60 petroleum ether

Sources & evidence

ORD record
ord-37e547226807464fb896a442f83eac94
Source dataset
uspto-grants-2013_07
Patent number
US08481544B2

Linked notes

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