Water → HCID 58379286, compound

HRID 1183001Notes

Reaction equation

HRID 1183001 reaction equation
[Cl:1][C:2]1[C:7]([C:8]([O:10][CH3:11])=[O:9])=[CH:6][CH:5]=[C:4](Cl)[N:3]=1.[Cl:13][C:14]1[CH:19]=[C:18]([Cl:20])[CH:17]=[CH:16][C:15]=1B(O)O.C(=O)([O-])[O-].[K+].[K+].O>C1COCC1.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.C(OCC)(=O)C>[Cl:1][C:2]1[C:7]([C:8]([O:10][CH3:11])=[O:9])=[CH:6][CH:5]=[C:4]([C:17]2[CH:16]=[CH:15][C:14]([Cl:13])=[CH:19][C:18]=2[Cl:20])[N:3]=1

Participants

8

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 2734659(2,4-Dichlorophenyl)boronic acidHCID 11106516Methyl 2,6-dichloropyridine-3-carboxylate

Product 1

HCID 58379286HCID 58379286, compound

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

6 g (29.12 mmol) of methyl 2,6-dichloropyridine-3-carboxylate, 5.56 g (29.12 mmol) of 2,4-dichlorophenylboronic acid, 12.07 g (87.4 mmol) of potassium carbonate and then 1.68 g (1.46 mmol) of tetrakis(triphenylphosphine)palladium(0) were initially charged in 120 ml of degassed THF, and the mixture was heated under reflux conditions and under an argon atmosphere for 16 h. 300 ml of water and 500 ml of ethyl acetate were added. After separating the phases and removing the solvent, the residue was chromatographed on silica gel (cyclohexane/ethyl acetate 6:1). 2.5 g (27% of theory) of the product were isolated in solid form.

Workup

  1. temperaturethe mixture was heated under reflux conditions and under an argon atmosphere for 16 h
  2. customAfter separating the phases
  3. customremoving the solvent
  4. customthe residue was chromatographed on silica gel (cyclohexane/ethyl acetate 6:1)
  5. custom2.5 g (27% of theory) of the product were isolated in solid form

Sources & evidence

ORD record
ord-86ad48ba7bbd4993aa801cf13c011e19
Source dataset
uspto-grants-2014_03
Patent number
US08664246B2

Reaction notes

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