Pyridine → methyl 6-fluoro-2-oxo-2,3-dihydro-1H-indole-5-carboxylate

HRID 241752

Reaction equation

HRID 241752 reaction equation
ClCC([C:5]1[CH:6]=[C:7]2[C:11](=[CH:12][C:13]=1[F:14])[NH:10][C:9](=[O:15])[CH2:8]2)=O.N1C=CC=C[CH:17]=1.[C:22](=[O:25])([O-])[O-:23].[K+].[K+].Cl.O1CCOCC1>>[F:14][C:13]1[CH:12]=[C:11]2[C:7]([CH2:8][C:9](=[O:15])[NH:10]2)=[CH:6][C:5]=1[C:22]([O:23][CH3:17])=[O:25]

Participants

5

Reactant 4

HCID 1049PyridineHCID 11430Potassium CarbonateHCID 106093595-(2-Chloroacetyl)-6-fluoroindolin-2-oneHCID 204431481,4-Dioxane hydrochloride

Product 1

HCID 66636241methyl 6-fluoro-2-oxo-2,3-dihydro-1H-indole-5-carboxylate

Procedure

A solution of the compound obtained in Step A (3.24 mmoles) in pyridine (99 mmol) is stirred at 90° C. for 2 hours. The reaction mixture is cooled to ambient temperature and then filtered. The solid obtained is washed with ethanol and dried in vacuo at 50° C. The compound is dissolved in MeOH (80 mL), and 0.434 mmol of potassium carbonate is added. The mixture is stirred at 80° C. for 5 hours. After cooling to ambient temperature, 4M HCl/dioxane solution is added (pH 3) and the mixture is evaporated to dryness. The residue obtained is triturated in water, filtered, washed with water and then dried in vacuo at 50° C. to yield the title product.

Workup

  1. filtrationfiltered
  2. customThe solid obtained
  3. washis washed with ethanol
  4. customdried in vacuo at 50° C
  5. dissolutionThe compound is dissolved in MeOH (80 mL)
  6. temperatureAfter cooling to ambient temperature
  7. customthe mixture is evaporated to dryness
  8. customThe residue obtained
  9. customis triturated in water
  10. filtrationfiltered
  11. washwashed with water
  12. customdried in vacuo at 50° C.

Sources & evidence

ORD record
ord-2e287565500145a9bb54513e67398a95
Source dataset
uspto-grants-2014_02
Patent number
US08653073B2

Linked notes

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