Ethanol → HCID 58326464, compound

HRID 2197408Notes

Reaction equation

HRID 2197408 reaction equation
Cl[C:2]1[N:3]=[N:4][C:5]([O:8][CH3:9])=[CH:6][CH:7]=1.C(=O)([O-])[O-].[Na+].[Na+].[CH2:16](O)[CH3:17].CCOC(C)=O.[C:25]1([CH3:31])[CH:30]=C[CH:28]=[CH:27][CH:26]=1>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>[CH3:31][C:25]1[CH:26]=[CH:27][CH:28]=[C:16]([CH3:17])[C:30]=1[C:2]1[N:3]=[N:4][C:5]([O:8][CH3:9])=[CH:6][CH:7]=1

Participants

7

Reactant 5

HCID 702EthanolHCID 1140TolueneHCID 8857Ethyl AcetateHCID 10340Sodium CarbonateHCID 744033-Chloro-6-methoxypyridazine

Product 1

HCID 58326464HCID 58326464, compound

Reagents, catalysts & solvents 1

HCID 178418397HCID 178418397, compoundCatalyst

Procedure

A mixture of 3-chloro-6-methoxy-pyridazine (1.44 g, 10 mmol), 2,6-methyl-phenyl boronic acid (1.73 g, 11.5 mmol), sodium carbonate (2 M aqueous solution, 10.5 ml, 21 mmol), ethanol (2 ml) and Pd(PPh3)4 (232 mg, 0.2 mmol) is refluxed in toluene (60 ml) overnight and then cooled to room temperature. EtOAc (20 ml) is added to the mixture and the organic layer is separated. The organic layer is washed with water, dried, and solvent removed. The crude product is purified by flash silica gel column (Hexanes/EtOAc 4:1) to give 3-(2,6-dimethyl-phenyl)-6-methoxy-pyridazine. 1H NMR: (CDCl3) 7.21-7.30 (m, 2H), 7.12 (d, 2H), 7.03 (d, 2H), 4.20 (s, 3H), 2.05 (s, 6H).

Workup

  1. customthe organic layer is separated
  2. washThe organic layer is washed with water
  3. customdried
  4. customsolvent removed
  5. customThe crude product is purified by flash silica gel column (Hexanes/EtOAc 4:1)

Sources & evidence

ORD record
ord-1fb81112742d4a9eb2718c47c8c88a6a
Source dataset
uspto-grants-2012_12
Patent number
US08338591B2

Reaction notes

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