Water → HCID 10108275, compound

HRID 2283241Notes

Reaction equation

HRID 2283241 reaction equation
Cl[C:2]1[N:3]=[N:4][CH:5]=[C:6]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[C:7]=1[C:8]([O:10][CH3:11])=[O:9].O.C(=O)([O-])[O-].[Na+].[Na+].[C:25]1(B(O)O)[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1>O1CCOCC1.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[C:25]1([C:2]2[N:3]=[N:4][CH:5]=[C:6]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)[C:7]=2[C:8]([O:10][CH3:11])=[O:9])[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1

Participants

7

Reactant 4

HCID 962WaterHCID 10340Sodium CarbonateHCID 66827Phenylboronic AcidHCID 86695671HCID 86695671, compound

Product 1

HCID 10108275HCID 10108275, compoundYield 86.1%

Reagents, catalysts & solvents 2

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

A solution of methyl 3-chloro-5-phenylpyridazine-4-carboxylate (300 mg, 1.20 mmol) in 1,4-dioxane (15 mL), distilled water (5 mL), sodium carbonate (256 mg, 2.41 mmol) and phenyl boronic acid (1.91 g, 1.57 mmol) were added and the reaction mixture was degassed for 10 min, followed by addition of tetrakis(triphenylphosphine) palladium (139 mg, 0.12 mmol) and refluxed at 100° C. for 12 h under argon atmosphere. After the completion of starting materials, the reaction mixture was cooled to rt and filtered through a celite pad to remove the solid impurities. The filtrate was diluted with ethyl acetate (40 mL), washed with aq NaHCO3 (5 mL×1), brine solution (5 mL×1) and dried over anhydrous Na2SO4. The organic extracts were evaporated under reduced pressure to obtain the crude product which was purified by column chromatography (100-200 mesh silica gel, 5% EtOAc in hexane) to furnish methyl 3,5-diphenylpyridazine-4-carboxylate (300 mg, 82%) as a white solid.

Workup

  1. additionwere added
  2. customthe reaction mixture was degassed for 10 min
  3. temperatureAfter the completion of starting materials, the reaction mixture was cooled to rt
  4. filtrationfiltered through a celite pad
  5. customto remove the solid impurities
  6. additionThe filtrate was diluted with ethyl acetate (40 mL)
  7. washwashed with aq NaHCO3 (5 mL×1), brine solution (5 mL×1)
  8. dry with materialdried over anhydrous Na2SO4
  9. customThe organic extracts were evaporated under reduced pressure
  10. customto obtain the crude product which
  11. customwas purified by column chromatography (100-200 mesh silica gel, 5% EtOAc in hexane)

Sources & evidence

ORD record
ord-df95281f3ddf47768cd3946619da88bd
Source dataset
uspto-grants-2015_09
Patent number
US09145372B2

Reaction notes

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