Sodium Carbonate → 3-Chloro-4-phenyl-6-pyridin-3-ylpyridazine

HRID 1674671Notes

Reaction equation

HRID 1674671 reaction equation
[C:1]1([C:7]2[CH:12]=[C:11](Cl)[N:10]=[N:9][C:8]=2[Cl:14])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[N:15]1[CH:20]=[CH:19][CH:18]=[C:17](B(O)O)[CH:16]=1.C([O-])([O-])=O.[Na+].[Na+]>O1CCOCC1.O>[Cl:14][C:8]1[N:9]=[N:10][C:11]([C:17]2[CH:16]=[N:15][CH:20]=[CH:19][CH:18]=2)=[CH:12][C:7]=1[C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 27343783-Pyridinylboronic acidHCID 113220803,6-Dichloro-4-phenylpyridazine

Product 1

HCID 591643703-Chloro-4-phenyl-6-pyridin-3-ylpyridazine

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
110 °C

Procedure

4-Phenyl-3,6-dichloropyridazine (1-1; 113 mg, 0.5 mmol) was dissolved in dry dioxane (2 mL). Then pyridine-3-boronic acid (99 mg, 0.8 mmol), 2 M aqueous Na2CO3 (0.75 mL) and palladium(0) tetrakis-triphenylphosphine (60 mg, 0.04 mmol) were added. This mixture was degassed, the vessel sealed and heated at 110° C. for 9 hours. The cooled reaction was diluted with water and the product mixture extracted into ethyl acetate, the extract dried over anhydrous NaSO4, filtered and evaporated. The product was purified by chromatography on silica gel and elution with a 20-70% ethyl acetate/hexane gradient to give 3-chloro-4-phenyl-6-pyridin-3-ylpyridazine (3-1). NMR (CDCl3): δ9.26 (1H, s), 8.78 (1H, d, J=4.6 Hz), 8.51 (1H, d, J=8 Hz), 7.86 (1H, s), 7.55-7.58 (5H, m), 7.51 (1H, dd, J=8 Hz, J=4.5 Hz); m/e (m+1): 268.1.

Workup

  1. customThis mixture was degassed
  2. customthe vessel sealed
  3. customThe cooled reaction
  4. extractionthe product mixture extracted into ethyl acetate
  5. dry with materialthe extract dried over anhydrous NaSO4
  6. filtrationfiltered
  7. customevaporated
  8. customThe product was purified by chromatography on silica gel and elution with a 20-70% ethyl acetate/hexane gradient

Sources & evidence

ORD record
ord-492f8ba1e43745d4a7d8b79235b051c1
Source dataset
uspto-grants-2011_08
Patent number
US08003643B2

Reaction notes

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