Sodium Carbonate → HCID 86683158, compound

HRID 920944Notes

Reaction equation

HRID 920944 reaction equation
Cl[C:2]1[C:7]2[C:8](=[O:12])[NH:9][N:10]=[CH:11][C:6]=2[N:5]=[CH:4][CH:3]=1.C([O-])([O-])=O.[Na+].[Na+].[N:19]1[CH:24]=[CH:23][C:22](B(O)O)=[CH:21][CH:20]=1.C([O-])(O)=O.[Na+]>C(O)C.C1(C)C=CC=CC=1.O.CC(=O)OCC.C(Cl)Cl.CO>[N:19]1[CH:24]=[CH:23][C:22]([C:2]2[C:7]3[C:8](=[O:12])[NH:9][N:10]=[CH:11][C:6]=3[N:5]=[CH:4][CH:3]=2)=[CH:21][CH:20]=1

Participants

10

Reactant 4

HCID 10340Sodium CarbonateHCID 516892Sodium BicarbonateHCID 2734379(Pyridin-4-yl)boronic acidHCID 86683159HCID 86683159, compound

Product 1

HCID 86683158HCID 86683158, compound

Reagents, catalysts & solvents 5

HCID 702EthanolSolventHCID 962WaterSolventHCID 1140TolueneSolventHCID 8857Ethyl AcetateSolventHCID 21226129Dichloromethane methanolSolvent

Conditions

Temperature
130 °C

Procedure

A reaction tube was charged with a solution of 4-chloropyrido[3,2-d]pyridazin-5(6H)-one (0.354 mmol) in 1 mL of ethanol and 1 mL of toluene under argon. To this suspension, a 2M solution of Na2CO3 (0.531 mmol) and pyridin-4-ylboronic acid (0.354 mmol) were added. Then, tetrakis(triphenylphoshine)palladium (0.035 mmol) was added. The reaction mixture was heated in a CEM microwave at about 130° C. for about 20 min. The reaction was monitored by TLC (DCM/methanol=9:1). After completion of the reaction, EA was added followed by the addition of water. The organic layer was basified with NaHCO3. The organic layers were dried over MgSO4, filtered, and concentrated under reduced pressure. The crude product was purified by column chromatography (25.2%).

Workup

  1. additionwas added
  2. dry with materialThe organic layers were dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customThe crude product was purified by column chromatography (25.2%)

Sources & evidence

ORD record
ord-6640c778e56c41d28c04b8895667a809
Source dataset
uspto-grants-2016_03
Patent number
US09273068B2

Reaction notes

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