Sodium Carbonate → 4-(5-Methoxy-3-pyridinyl)benzonitrile

HRID 1685403Notes

Reaction equation

HRID 1685403 reaction equation
Br[C:2]1[CH:3]=[N:4][CH:5]=[C:6]([O:8][CH3:9])[CH:7]=1.[C:10]([C:12]1[CH:17]=[CH:16][C:15](B(O)O)=[CH:14][CH:13]=1)#[N:11].[Cl-].[Li+].C(=O)([O-])[O-].[Na+].[Na+]>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.C(OCC)(=O)C.O.CO.C1(C)C=CC=CC=1>[CH3:9][O:8][C:6]1[CH:7]=[C:2]([C:15]2[CH:16]=[CH:17][C:12]([C:10]#[N:11])=[CH:13][CH:14]=2)[CH:3]=[N:4][CH:5]=1

Participants

10

Reactant 4

HCID 10340Sodium CarbonateHCID 433294Lithium ChlorideHCID 8171633-Bromo-5-methoxypyridineHCID 27343264-Cyanophenylboronic acid

Product 1

HCID 672914774-(5-Methoxy-3-pyridinyl)benzonitrileYield 89%

Reagents, catalysts & solvents 5

HCID 178418397HCID 178418397, compoundCatalystHCID 887MethanolSolventHCID 962WaterSolventHCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Procedure

1.93 g (10.3 mM) of 3-bromo-5-methoxypyridine and 1.85 g (12.36 mM) of 4-cyanophenylboronic acid are mixed with 40 ml of toluene and 40 ml of methanol. 0.6 g (0.5 mM) of tetrakis(triphenylphosphine)palladium and 1.3 g (30.9 mM) of lithium chloride are added. 26 ml of 1 M sodium carbonate solution are then added. The mixture is refluxed for 5 hours and, after cooling, water and ethyl acetate are added to the reaction medium. The aqueous phase is separated off and extracted with ethyl acetate. The combined organic phases are dried over magnesium sulfate and then concentrated under reduced pressure. The evaporation residue is purified by chromatography on silica gel using a dichloromethane/ethyl acetate mixture (94/6; v/v) as the eluent to give the expected product in the form of a beige solid with a yield of 89%.

Workup

  1. temperatureThe mixture is refluxed for 5 hours
  2. temperatureafter cooling
  3. customThe aqueous phase is separated off
  4. extractionextracted with ethyl acetate
  5. dry with materialThe combined organic phases are dried over magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe evaporation residue is purified by chromatography on silica gel using a dichloromethane/ethyl acetate mixture (94/6; v/v) as the eluent

Sources & evidence

ORD record
ord-6fe4c18ad00544e98a7a30d0911a6d3c
Source dataset
uspto-grants-2012_04
Patent number
US08148407B2

Reaction notes

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