Potassium Phosphate, Tribasic → HCID 58382525, compound

HRID 1027487Notes

Reaction equation

HRID 1027487 reaction equation
Br[CH2:2][C:3]1[N:4]=[C:5]([O:19][CH2:20][CH2:21][CH3:22])[C:6]2[N:11]=[C:10]([C:12]3[CH:17]=[CH:16][CH:15]=[C:14]([F:18])[CH:13]=3)[O:9][C:7]=2[N:8]=1.[F:23][C:24]([F:35])([F:34])[C:25]1[CH:30]=[CH:29][C:28](B(O)O)=[CH:27][CH:26]=1.P([O-])([O-])([O-])=O.[K+].[K+].[K+].C1(P(C2CCCCC2)C2CCCCC2)CCCCC1>C1(C)C=CC=CC=1>[F:18][C:14]1[CH:13]=[C:12]([C:10]2[O:9][C:7]3[N:8]=[C:3]([CH2:2][C:28]4[CH:29]=[CH:30][C:25]([C:24]([F:35])([F:34])[F:23])=[CH:26][CH:27]=4)[N:4]=[C:5]([O:19][CH2:20][CH2:21][CH3:22])[C:6]=3[N:11]=2)[CH:17]=[CH:16][CH:15]=1

Participants

6

Reactant 4

HCID 62657Potassium Phosphate, TribasicHCID 75806TricyclohexylphosphineHCID 27343894-(Trifluoromethyl)phenylboronic acidHCID 67176028HCID 67176028, compound

Product 1

HCID 58382525HCID 58382525, compoundYield 13.3%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

146.5 mg of 5-bromomethyl-2-(3-fluoro-phenyl)-7-propoxy-oxazolo[5,4-d]pyrimidine and 114 mg of 4-trifluoromethyl-benzeneboronic acid were dissolved in 3 ml of toluene. 170 mg of tripotassium phosphate and 11.2 mg of tricyclohexylphosphine were added, and argon was bubbled through the mixture for 10 min. Then 4.5 mg of palladium(II) acetate were added, and the reaction mixture was heated to reflux for 8 h under argon. After cooling, ethyl acetate and water were added. The mixture was filtered through a ChemElut cartridge and the cartridge washed with ethyl acetate. The combined filtrates were evaporated in vacuo and the residue purified by preparative HPLC (method HPLC2). 23 mg of the title compound were obtained.

Workup

  1. customargon was bubbled through the mixture for 10 min
  2. additionThen 4.5 mg of palladium(II) acetate were added
  3. temperaturethe reaction mixture was heated
  4. temperatureto reflux for 8 h under argon
  5. temperatureAfter cooling
  6. additionethyl acetate and water were added
  7. filtrationThe mixture was filtered through a ChemElut cartridge
  8. washthe cartridge washed with ethyl acetate
  9. customThe combined filtrates were evaporated in vacuo
  10. customthe residue purified by preparative HPLC (method HPLC2)

Sources & evidence

ORD record
ord-d10bb270b5b449fc8978588151460e8f
Source dataset
uspto-grants-2014_05
Patent number
US08735387B2

Reaction notes

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