1,4-Dioxane → HCID 24771820, compound

HRID 1529475Notes

Reaction equation

HRID 1529475 reaction equation
P(O)(O)(O)=O.[S:6]1[C:14]2[CH:13]=[CH:12][N:11]=[CH:10][C:9]=2[CH:8]=[C:7]1B(O)O.[CH3:18][C:19]1[CH:23]=[N:22][N:21]([C:24]2[CH:29]=[CH:28][CH:27]=[C:26]([CH3:30])[N:25]=2)[C:20]=1OS(C(F)(F)F)(=O)=O.[O-]P([O-])([O-])=O.[K+].[K+].[K+].O1CCOCC1>C(OCC)(=O)C.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2].C1(P(C2C=CC=CC=2)[C-]2C=CC=C2)C=CC=CC=1.[C-]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C1.[Fe+2]>[CH3:18][C:19]1[CH:23]=[N:22][N:21]([C:24]2[CH:29]=[CH:28][CH:27]=[C:26]([CH3:30])[N:25]=2)[C:20]=1[C:7]1[S:6][C:14]2[CH:13]=[CH:12][N:11]=[CH:10][C:9]=2[CH:8]=1

Participants

8

Reactant 4

HCID 312751,4-DioxaneHCID 62657Potassium Phosphate, TribasicHCID 67246246HCID 67246246, compoundHCID 86619681HCID 86619681, compound

Product 1

HCID 24771820HCID 24771820, compound

Reagents, catalysts & solvents 3

HCID 635956Ferrocene-1,1'-bis-(diphenylphosphine)CatalystHCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 8857Ethyl AcetateSolvent

Procedure

An oven-dried three-neck round-bottom flask equipped with reflux condenser and gas inlet valve was charged with thieno[3,2-c]pyridine-2-boronic acid trihydrogen phosphate (1.0 g), trifluoro-methanesulfonic acid 4-methyl-2-(6-methyl-pyridin-2-yl)-2H-pyrazol-3-yl ester (1.16 g), potassium phosphate tribasic (2.3 g), 1,4-dioxane (30 mL), dichloro[1,1′-bis(diphenylphosphino)ferrocene]palladium (II) dichloromethane adduct (0.60 g), and 1,1′-bis(diphenylphosphino)ferrocene (0.40 g) and the stirring mixture was brought to reflux under a nitrogen atmosphere for 18 hours. The reaction mixture was diluted with ethyl acetate (250 mL) and the solution was treated with activated carbon and filtered through Celite. The filtrate was concentrated under reduced pressure and the concentrate was purified by silica gel chromatography.

Workup

  1. customAn oven-dried three-neck round-bottom flask equipped
  2. temperaturewith reflux condenser and gas inlet valve
  3. temperatureto reflux under a nitrogen atmosphere for 18 hours
  4. additionthe solution was treated with activated carbon
  5. filtrationfiltered through Celite
  6. concentrationThe filtrate was concentrated under reduced pressure
  7. customthe concentrate was purified by silica gel chromatography

Sources & evidence

ORD record
ord-62fa5a79120746f3b80783e7f042355c
Source dataset
uspto-grants-2015_07
Patent number
US09090625B2

Reaction notes

Loading…