Methanol → HCID 12993699, compound

HRID 1837445Notes

Reaction equation

HRID 1837445 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([C:8]2[O:12][CH:11]=[N:10][CH:9]=2)[N:5]=[C:4](Cl)[C:3]=1[Cl:14].[C:15]([O-:18])(=[O:17])C.[Na+].[C]=O.[CH3:22]O>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C1(P(C2C=CC=CC=2)CCCCP(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[NH2:1][C:2]1[CH:7]=[C:6]([C:8]2[O:12][CH:11]=[N:10][CH:9]=2)[N:5]=[C:4]([C:15]([O:18][CH3:22])=[O:17])[C:3]=1[Cl:14]

Participants

7

Reactant 4

HCID 887MethanolHCID 517045Sodium AcetateHCID 12993698HCID 12993698, compoundHCID 178418416HCID 178418416, compound

Product 1

HCID 12993699HCID 12993699, compound

Reagents, catalysts & solvents 2

HCID 821241,4-Bis(diphenylphosphino)butaneCatalystHCID 167845palladium(II) acetateCatalyst

Procedure

A solution of 4-amino-2,3-dichloro-6-(5-oxazolyl)pyridine (800 mg, 3.48 mmol), sodium acetate (571 mg, 6.96 mmol), palladium acetate (16 mg, 0.07 mmol), and 1,4-bis(diphenylphosphino)butane (30 mg, 0.07 mmol) in methanol (25 mL) was pressurized with carbon monoxide at 100 psi. After 12 hours at 100° C., the reaction mixture was cooled and concentrated. The residue was taken up into ethyl actetate and washed twice with water. The organic layer was dried (MgSO4) and concentrated to provide methyl 4-amino-3-chloro-6-(5-oxazolyl)pyridine-2-carboxylate (788 mg, 3.10 mmol), mp 166-70° C.

Workup

  1. temperaturethe reaction mixture was cooled
  2. concentrationconcentrated
  3. washwashed twice with water
  4. dry with materialThe organic layer was dried (MgSO4)
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-c58f062e7b674d449002cab98030791b
Source dataset
uspto-grants-2004_08
Patent number
US06784137B2

Reaction notes

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