Sodium Carbonate → HCID 67292314, compound

HRID 1685402Notes

Reaction equation

HRID 1685402 reaction equation
I[C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][N:3]=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.C1(C)C=CC=CC=1.CO>[CH3:9][O:8][C:5]1[CH:6]=[CH:7][C:2]([C:15]2[CH:16]=[CH:17][C:12]([C:10]#[N:11])=[CH:13][CH:14]=2)=[N:3][CH:4]=1

Participants

8

Reactant 4

HCID 10340Sodium CarbonateHCID 433294Lithium ChlorideHCID 27343264-Cyanophenylboronic acidHCID 70107332-Iodo-5-methoxypyridine

Product 1

HCID 67292314HCID 67292314, compoundYield 66%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 887MethanolSolventHCID 1140TolueneSolvent

Procedure

A mixture of 3.1 g (13.2 mM) of 2-iodo-5-methoxypyridine, 2.9 g (19.8 mM) of 4-cyanophenylboronic acid, 1.7 g (40 mM) of lithium chloride, 0.6 g (0.52 mM) of tetrakis(triphenylphosphine)palladium, 30 ml of methanol and 30 ml of toluene is prepared and 20 ml (40 mM) of 2 M sodium carbonate are added. The reaction mixture is heated at the reflux temperature of the solvent for 72 hours. The phases are separated and the aqueous phase is extracted with ethyl acetate. The combined organic phases are washed with N sodium hydroxide solution, with water and with saturated sodium chloride solution and then dried over magnesium sulfate. After evaporation of the solvents, the crude product is purified by chromatography on silica gel using dichloromethane as the eluent to give the expected product in the form of a pale yellow solid with a yield of 66%.

Workup

  1. customis prepared
  2. temperatureThe reaction mixture is heated at the reflux temperature of the solvent for 72 hours
  3. customThe phases are separated
  4. extractionthe aqueous phase is extracted with ethyl acetate
  5. washThe combined organic phases are washed with N sodium hydroxide solution, with water and with saturated sodium chloride solution
  6. dry with materialdried over magnesium sulfate
  7. customAfter evaporation of the solvents
  8. customthe crude product is purified by chromatography on silica gel

Sources & evidence

ORD record
ord-3df177d7955040668f2d06dcd38c31dd
Source dataset
uspto-grants-2012_04
Patent number
US08148407B2

Reaction notes

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