Sodium Carbonate → Methyl 3-(6-oxo-1,6-dihydropyridazin-4-yl)benzoate

HRID 407073Notes

Reaction equation

HRID 407073 reaction equation
Cl[C:2]1[CH2:3][C:4](=[O:8])[N:5]=[N:6][CH:7]=1.[CH3:9][O:10][C:11]([C:13]1[CH:14]=[C:15](B(O)O)[CH:16]=[CH:17][CH:18]=1)=[O:12].C(=O)([O-])[O-].[Na+].[Na+]>O1CCOCC1.O.Cl[Pd](Cl)(P(C(C)(C)C)(C(C)(C)C)C1C=CC(N(C)C)=CC=1)P(C1C=CC(N(C)C)=CC=1)(C(C)(C)C)C(C)(C)C>[O:8]=[C:4]1[NH:5][N:6]=[CH:7][C:2]([C:17]2[CH:18]=[C:13]([CH:14]=[CH:15][CH:16]=2)[C:11]([O:10][CH3:9])=[O:12])=[CH:3]1

Participants

7

Reactant 3

HCID 10340Sodium CarbonateHCID 27347143-(Methoxycarbonyl)benzeneboronic acidHCID 679801625-chloropyridazin-3(4H)-one

Product 1

HCID 67980034Methyl 3-(6-oxo-1,6-dihydropyridazin-4-yl)benzoate

Reagents, catalysts & solvents 3

HCID 178482906HCID 178482906, compoundCatalystHCID 962WaterSolvent2×HCID 312751,4-DioxaneSolvent2×

Conditions

Temperature
95 °C

Procedure

Dichloro(bis{di-tert-butyl[4-(dimethylamino)phenyl]phosphoranyl})palladium (85 mg, 0.12 mmol) was added to a mixture of 5-chloropyridazin-3(4H)-one (0.52 g, 4.0 mmol, Maybridge, Cat. No. MO08305), [3-(methoxycarbonyl)phenyl]boronic acid (0.864 g, 4.80 mmol, Aldrich, Cat. No. 591130) and sodium carbonate (0.85 g, 8.0 mmol) in 1,4-dioxane (9 mL) and water (1 mL). The reaction mixture was vacuumed and refilled with nitrogen 3 times. The reaction was stirred at 95° C. overnight. To this reaction mixture was added dioxane (3.0 ml) and water (10 ml) and then filtered, washed with acetonitrile/water, dried to provide the pure product (0.86 g). LCMS (M+H)+: m/z=231.1

Workup

  1. additionrefilled with nitrogen 3 times
  2. filtrationfiltered
  3. washwashed with acetonitrile/water
  4. customdried

Sources & evidence

ORD record
ord-7c8ab59a606641a88efc54e75b13fc91
Source dataset
uspto-grants-2014_06
Patent number
US08754114B2

Reaction notes

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