Sodium Carbonate → HCID 136069467, compound

HRID 880374Notes

Reaction equation

HRID 880374 reaction equation
Cl[C:2]1[C:3](=[O:17])[N:4]([CH:9]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH3:10])[N:5]=[CH:6][C:7]=1Cl.[C:18](=[O:21])([O-])[O-].[Na+].[Na+].[OH:24][C:25]1[CH:30]=[CH:29][C:28](B(O)O)=[CH:27][CH:26]=1>C1(C)C=CC=CC=1.C(O)C.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>[OH:24][C:25]1[CH:30]=[CH:29][C:28]([C:2]2[C:3](=[O:17])[N:4]([CH:9]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)[CH3:10])[N:5]=[CH:6][C:7]=2[C:11]2[CH:12]=[CH:13][C:18]([OH:21])=[CH:10][CH:9]=2)=[CH:27][CH:26]=1

Participants

7

Reactant 3

HCID 10340Sodium CarbonateHCID 27343604-Hydroxyphenylboronic acid2×HCID 680139864,5-dichloro-2-(1-phenylethyl)pyridazin-3(2H)-one

Product 1

HCID 136069467HCID 136069467, compoundYield 78%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 702EthanolSolventHCID 1140TolueneSolvent

Conditions

Temperature
80 °C

Procedure

the intermediate 1a (8.7 g, 32.3 mmol) is placed in presence of tetrakis(triphenylphosphine)palladium(0) (1.12 g, 0.97 mmol) and sodium carbonate (6.85 g, 64.7 mmol) in a mixture of 50 mL of toluene and 50 mL of ethanol and the mixture is heated to 80° C. 1.2 equivalent of 4-hydroxyphenylboronic acid is added and the mixture is heated under reflux for 5 h and 1.2 additional equivalent of 4-hydroxyphenylboronic acid is added and the reflux is maintained throughout the night. Following concentration to dryness, the residue is taken up with water and is extracted using AcOEt. After drying the organic layers and concentration to dryness, the residue obtained is purified by flash chromatography (CH2Cl2-MeOH, gradient 100-0 to 97-3 over 40 min.). 0.7g of minority compound 1 is obtained and 8.2g of solid corresponding to the majority substituted mono product 4-chloro-5-(4-hydroxyphenyl)-2-(1-phenylethyl)-pyridazin-3(2H)-one is obtained (yield:78%).

Workup

  1. temperaturethe mixture is heated
  2. temperatureunder reflux for 5 h
  3. temperaturethe reflux is maintained throughout the night
  4. concentrationconcentration to dryness
  5. extractionis extracted
  6. customAfter drying
  7. concentrationthe organic layers and concentration to dryness
  8. customthe residue obtained
  9. customis purified by flash chromatography (CH2Cl2-MeOH, gradient 100-0 to 97-3 over 40 min.)

Sources & evidence

ORD record
ord-49ca810266e94e16b55c5c6a96be41bb
Source dataset
uspto-grants-2015_03
Patent number
US08993569B2

Reaction notes

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