Potassium Carbonate → 6-(3,4-Dimethoxyphenyl)-3-nitropyridine-2-carbonitrile

HRID 1517396Notes

Reaction equation

HRID 1517396 reaction equation
Cl[C:2]1[N:7]=[C:6]([C:8]#[N:9])[C:5]([N+:10]([O-:12])=[O:11])=[CH:4][CH:3]=1.[CH3:13][O:14][C:15]1[CH:16]=[C:17](B(O)O)[CH:18]=[CH:19][C:20]=1[O:21][CH3:22].C(=O)([O-])[O-].[K+].[K+]>C1(C)C=CC=CC=1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH3:13][O:14][C:15]1[CH:16]=[C:17]([C:2]2[N:7]=[C:6]([C:8]#[N:9])[C:5]([N+:10]([O-:12])=[O:11])=[CH:4][CH:3]=2)[CH:18]=[CH:19][C:20]=1[O:21][CH3:22]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 27347023,4-Dimethoxyphenylboronic acidHCID 133817056-Chloro-3-nitropyridine-2-carbonitrile

Product 1

HCID 688404046-(3,4-Dimethoxyphenyl)-3-nitropyridine-2-carbonitrileYield 79.3%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 1140TolueneSolvent

Procedure

To a degassed suspension of 6-chloro-2-cyano-3-nitropyridine (5.51 g, 30 mmol), 3,4-dimethoxyphenyl boronic acid (6.55 g, 36 mmole) and potassium carbonate (16.59 g, 120 mmol) in dry toluene (300 ml), was added a catalytic amount of tetrakis(triphenylphosphine)palladium (3.47 g, 3 mmol). The mixture was refluxed for 24 hours and after cooling, the volatiles were evaporated to dryness. The crude mixture was purified by silica gel column chromatography, the mobile phase consisting of hexane/CH2Cl2 mixtures (in a ratio gradually ranging from 15:85 to 0:100). The appropriated fractions were collected, evaporated to dryness and the residue was suspended in ether. The orange precipitate was filtered off, washed with ether and dried, resulting in the pure title compound (6.79 g, yield 79%).

Workup

  1. temperatureThe mixture was refluxed for 24 hours
  2. temperatureafter cooling
  3. customthe volatiles were evaporated to dryness
  4. customThe crude mixture was purified by silica gel column chromatography
  5. customThe appropriated fractions were collected
  6. customevaporated to dryness
  7. filtrationThe orange precipitate was filtered off
  8. washwashed with ether
  9. customdried

Sources & evidence

ORD record
ord-103970717bc54be9a41e39aab93d3718
Source dataset
uspto-grants-2012_07
Patent number
US08232278B2

Reaction notes

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