Sodium Carbonate → HCID 69159599, compound

HRID 2117331Notes

Reaction equation

HRID 2117331 reaction equation
Cl[C:2]1[CH:7]=[N:6][NH:5][C:4](=[O:8])[CH:3]=1.B1(B2OC(C)(C)C(C)(C)O2)OC(C)(C)C(C)(C)O1.C([O-])(=O)C.[K+].Br[C:33]1[CH:38]=[CH:37][C:36]([C:39]([F:42])([F:41])[F:40])=[CH:35][C:34]=1[F:43].C(=O)([O-])[O-].[Na+].[Na+]>C(OCC)(=O)C.Cl[Pd]Cl.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].O1CCOCC1>[F:43][C:34]1[CH:35]=[C:36]([C:39]([F:40])([F:41])[F:42])[CH:37]=[CH:38][C:33]=1[C:2]1[CH:7]=[N:6][NH:5][C:4](=[O:8])[CH:3]=1

Participants

9

Reactant 5

HCID 10340Sodium CarbonateHCID 1424144-Bromo-3-fluorobenzotrifluorideHCID 517044Potassium AcetateHCID 2733548Bis(pinacolato)diboraneHCID 199057185-Chloropyridazin-3(2H)-one

Product 1

HCID 69159599HCID 69159599, compoundYield 21.1%

Reagents, catalysts & solvents 3

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of 5-chloropyridazin-3(2H)-one (1.91 g, 14.6 mmol), bis(pinacolato)diboron (3.89 g, 15.3 mmol), potassium acetate (2.14 g, 21.8 mmol), dioxane (100 ml) and [1,1′-bis(diphenylphosphino)ferrocene]-dichloropalladium (0.4 g) was degassed (N2), then heated at 90° C. for 16 hours under nitrogen. More catalyst (0.45 g) was added and the mixture heated 7 hours more. After cooling to room temperature 4-bromo-3-fluorobenzotrifluoride (4.5 g, 18.5 mmol) was added along with 2M aqueous sodium carbonate solution (35 ml) and a further portion of catalyst (450 mg). The mixture was heated to 115° C. for 24 h, then cooled to room temperature, diluted with ethyl acetate (250 ml) and filtered. The layers were separated, the aqueous phase extracted with ethyl acetate (100 ml) and the combined organic layers evaporated. The residue was purified by flash column chromatography eluting with 5% methanol in dichloromethane to give the title compound (795 mg, 21%).

Workup

  1. customwas degassed (N2)
  2. additionMore catalyst (0.45 g) was added
  3. temperaturethe mixture heated 7 hours more
  4. temperatureThe mixture was heated to 115° C. for 24 h
  5. temperaturecooled to room temperature
  6. filtrationfiltered
  7. customThe layers were separated
  8. extractionthe aqueous phase extracted with ethyl acetate (100 ml)
  9. customthe combined organic layers evaporated
  10. customThe residue was purified by flash column chromatography
  11. washeluting with 5% methanol in dichloromethane

Sources & evidence

ORD record
ord-a61edb5818414cbda0f42fe4523fb546
Source dataset
uspto-grants-2008_10
Patent number
US07442701B2

Reaction notes

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