Potassium Phosphate, Tribasic → HCID 68639392, compound

HRID 2196443Notes

Reaction equation

HRID 2196443 reaction equation
[O-]P([O-])([O-])=O.[K+].[K+].[K+].[O:9]1[CH:13]=[CH:12][C:11](B(O)O)=[CH:10]1.[Si:17]([O:24][CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=1[C:32]1[CH:33]=[CH:34][C:35]2[N:36]([CH:38]=[C:39](Cl)[N:40]=2)[CH:37]=1)([C:20]([CH3:23])([CH3:22])[CH3:21])([CH3:19])[CH3:18]>C(O)C.C1(C)C=CC=CC=1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C1(P(C2CCCCC2)C2C=CC=CC=2C2C(OC)=CC=CC=2OC)CCCCC1>[Si:17]([O:24][CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=1[C:32]1[CH:33]=[CH:34][C:35]2[N:36]([CH:38]=[C:39]([C:11]3[CH:12]=[CH:13][O:9][CH:10]=3)[N:40]=2)[CH:37]=1)([C:20]([CH3:23])([CH3:21])[CH3:22])([CH3:19])[CH3:18]

Participants

8

Reactant 3

HCID 62657Potassium Phosphate, TribasicHCID 2734358Furan-3-boronic acidHCID 44232376HCID 44232376, compound

Product 1

HCID 68639392HCID 68639392, compoundYield 99.1%

Reagents, catalysts & solvents 4

HCID 702EthanolCatalystHCID 167845palladium(II) acetateCatalystHCID 112698722-Dicyclohexylphosphino-2',6'-dimethoxybiphenylCatalystHCID 1140TolueneSolvent

Conditions

Temperature
115 °C

Procedure

3 mg of palladium acetate, 11 mg of 2-(dicyclohexyl)phosphino-2′,6′-dimethoxy-1,1′-biphenyl, 270 mg of K3PO4, 110 mg of 3-furanboronic acid and a few drops of ethanol are placed in a reactor containing a mixture of 240 mg of 6-[2-[(tert-butyldimethylsilanyl)oxymethyl]phenyl]-2-chloroimidazo[1,2-a]pyridine in 2 ml of toluene degassed beforehand under an argon stream. The reactor is closed and heated at 115° C. for 16 h. After cooling, the reaction mixture is filtered through celite, washed with dichloromethane and then concentrated under reduced pressure. The residue is purified by silica gel chromatography, elution being carried out with a dichloromethane/methanol mixture. 258 mg of compound are obtained.

Workup

  1. additioncontaining
  2. customThe reactor is closed
  3. temperatureAfter cooling
  4. filtrationthe reaction mixture is filtered through celite
  5. washwashed with dichloromethane
  6. concentrationconcentrated under reduced pressure
  7. customThe residue is purified by silica gel chromatography, elution

Sources & evidence

ORD record
ord-03cee4302f7541d0bd249c925f759d19
Source dataset
uspto-grants-2012_12
Patent number
US08338451B2

Reaction notes

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