Pyridine → HCID 67530877, compound

HRID 2068741Notes

Reaction equation

HRID 2068741 reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][C:10]=1[NH2:11])[NH:7][C:6](=[O:12])[CH2:5]2.N1C=CC=CC=1.[CH3:19][O:20][CH2:21][C:22](Cl)=[O:23]>O1CCCC1>[F:1][C:2]1[C:10]([NH:11][C:22](=[O:23])[CH2:21][O:20][CH3:19])=[CH:9][C:8]2[C:4](=[CH:5][C:6](=[O:12])[N:7]=2)[CH:3]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 96623Methoxyacetyl chlorideHCID 101035046-Amino-5-fluoroindolin-2-one

Product 1

HCID 67530877HCID 67530877, compoundYield 40.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

5-Fluoro-6-Amino-indol-2-one 9d (2.028 g, 12.2 mmol) was dissolved in 30 mL of tetrahydrofuran under stirring at room temperature, and 1.3 mL of pyridine was then added to the solution. The reaction system was cooled down to −50° C. in a dry ice-ethanol bath. Methoxy-acetyl chloride (1.35 g, 12.5 mmol) was dissolved in 20 mL of tetrahydrofuran under stirring, and the solution was then added dropwise to the above reaction system. Upon completion of the addition, the dry ice-ethanol bath was removed. The reaction system was allowed to warm up to room temperature and stirred overnight until TLC showed the disappearance of starting materials. The resulting solid was filtered, washed with water (10 mL ×3) and recrystallized from methanol to give the title compound 5-fluoro-6-methoxyacetamido-2-oxoindole 13a (1.18 g, yield 40.6%) as a gray solid.

Workup

  1. temperatureThe reaction system was cooled down to −50° C. in a dry ice-ethanol bath
  2. stirringunder stirring
  3. additionthe solution was then added dropwise to the above reaction system
  4. additionUpon completion of the addition
  5. customthe dry ice-ethanol bath was removed
  6. temperatureto warm up to room temperature
  7. stirringstirred overnight until TLC
  8. filtrationThe resulting solid was filtered
  9. washwashed with water (10 mL ×3)
  10. customrecrystallized from methanol

Sources & evidence

ORD record
ord-54bb86e3c1714a44b3db0e098e5df4dd
Source dataset
uspto-grants-2012_10
Patent number
US08299069B2

Reaction notes

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