Potassium Phosphate, Tribasic → HCID 44230454, compound

HRID 2196438Notes

Reaction equation

HRID 2196438 reaction equation
Cl[C:2]1[N:3]=[C:4]2[CH:9]=[CH:8][C:7]([C:10]3[CH:11]=[C:12]([CH2:16][OH:17])[CH:13]=[CH:14][CH:15]=3)=[CH:6][N:5]2[CH:18]=1.[N:19]1[C:28]2[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=2)[CH:22]=[C:21](B(O)O)[CH:20]=1.C1(P(C2CCCCC2)C2C=CC=CC=2C2C(OC)=CC=CC=2OC)CCCCC1.[O-]P([O-])([O-])=O.[K+].[K+].[K+]>C1(C)C=CC=CC=1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[N:19]1[C:28]2[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=2)[CH:22]=[C:21]([C:2]2[N:3]=[C:4]3[CH:9]=[CH:8][C:7]([C:10]4[CH:11]=[C:12]([CH2:16][OH:17])[CH:13]=[CH:14][CH:15]=4)=[CH:6][N:5]3[CH:18]=2)[CH:20]=1

Participants

7

Reactant 4

HCID 62657Potassium Phosphate, TribasicHCID 2734663Quinoline-3-boronic acidHCID 112698722-Dicyclohexylphosphino-2',6'-dimethoxybiphenylHCID 44232374HCID 44232374, compound

Product 1

HCID 44230454HCID 44230454, compoundYield 12%

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 1140TolueneSolvent

Procedure

In a screw reactor, 550 mg of [3-(2-chloroimidazo[1,2-a]pyridin-6-yl)phenyl]methanol, 550 mg of 3-quinolineboronic acid, 20 mg of palladium acetate, 70 mg of 2-dicyclohexylphosphino-2′,6′-dimethoxy-1,1′-biphenyl and 900 mg of K3PO4 are placed in 8 ml of anhydrous toluene. The reactor is closed and heating is carried out at 115° C. for 16 h. After cooling, the reaction mixture is filtered through celite and rinsed with dichloromethane. The organic phase is washed with a saturated solution of NaCl, and then separated, dried and concentrated under reduced pressure. The residue is purified by silica gel chromatography, elution being carried out with a dichloromethane/methanol mixture. 90 mg of compound are obtained.

Workup

  1. customThe reactor is closed
  2. temperatureheating
  3. temperatureAfter cooling
  4. filtrationthe reaction mixture is filtered through celite
  5. washrinsed with dichloromethane
  6. washThe organic phase is washed with a saturated solution of NaCl
  7. customseparated
  8. customdried
  9. concentrationconcentrated under reduced pressure
  10. customThe residue is purified by silica gel chromatography, elution

Sources & evidence

ORD record
ord-35c9b99f60b44b32a894f9b1b1765876
Source dataset
uspto-grants-2012_12
Patent number
US08338451B2

Reaction notes

Loading…