Sodium Carbonate → 3-Bromo-6-(2-fluoro-phenyl)-pyridazine

HRID 1931379Notes

Reaction equation

HRID 1931379 reaction equation
[Br:1][C:2]1[N:3]=[N:4][C:5](Br)=[CH:6][CH:7]=1.[F:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1B(O)O.C(=O)([O-])[O-].[Na+].[Na+]>COCCOC.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[Br:1][C:2]1[N:3]=[N:4][C:5]([C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=2[F:9])=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 2488523,6-DibromopyridazineHCID 27343542-Fluorophenylboronic acid

Product 1

HCID 457878323-Bromo-6-(2-fluoro-phenyl)-pyridazine

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 80711,2-DimethoxyethaneSolvent

Procedure

300 mg (1.26 mmol) of 3,6-dibromopyridazine, 176.5 mg (1.26 mmol) 2-fluoro-phenylboronic acid, 34.7 mg (0.038 mmol) of tetrakis(triphenylphosphine)palladium and 1.26 ml of an aqueous 1 M sodium carbonate solution in 15 ml of DME were heated under reflux for 3 h. After cooling, the reaction mixture was poured onto water and extracted with ethyl acetate. The combined organic phases were dried, evaporated, and the product purified by RP18 chromatography. Yield: 62 mg.

Workup

  1. temperatureunder reflux for 3 h
  2. temperatureAfter cooling
  3. additionthe reaction mixture was poured onto water
  4. extractionextracted with ethyl acetate
  5. customThe combined organic phases were dried
  6. customevaporated
  7. customthe product purified by RP18 chromatography

Sources & evidence

ORD record
ord-59d79e731dcb4cc8a6208df2f2f4900b
Source dataset
uspto-grants-2012_05
Patent number
US08188291B2

Reaction notes

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