Acetyl chloride → N-(5-Fluoro-2-oxo-2,3-dihydro-1H-indol-6-yl)acetamide

HRID 1811200Notes

Reaction equation

HRID 1811200 reaction equation
[NH2:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6](=CC3NC4CCN(CCN(CC)CC)C(=O)C=4C=3C)[C:7](=[O:11])[NH:8]2)=[CH:4][C:3]=1[F:31].[C:32](Cl)(=[O:34])[CH3:33]>O1CCCC1>[F:31][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][C:2]=1[NH:1][C:32](=[O:34])[CH3:33])[NH:8][C:7](=[O:11])[CH2:6]2

Participants

4

Reactant 2

HCID 6367Acetyl chlorideHCID 666072882-(6-Amino-5-fluoro-2-oxo-1,2-dihydro-indol-3-ylidenemethyl)-5-(2-diethylamino-ethyl)-3-methyl-1,5,6,7-tetrahydro-pyrrolo[3,2-c]pyridin-4-one

Product 1

HCID 45118150N-(5-Fluoro-2-oxo-2,3-dihydro-1H-indol-6-yl)acetamideYield 100.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

A stirred solution of 6-amino-5-fluoro-1,3-dihydro-indol-2-one (1.0 g, 6 mmol) obtained from Example 7 in 30 ml of tetrahydrofuran was added with tirethylamine (1.3 ml, 9 mmol). The solution was cooled down to 0° C. in an ice-water bath and added with acetyl chloride (1.3 ml, 9 mmol) dropwise. Upon the completion of the addition, the resulting mixture was heated to reflux for 1.5 hours and cooled until precipitate was formed. The solid was filtered, washed with water (50 ml×3) and dried in vacuo to give N-(5-fluoro-2-oxo-2,3-dihydro-1H-indol-6-yl)-acetamide (1.25 g, 99%) as a white solid.

Workup

  1. additionUpon the completion of the addition
  2. temperaturethe resulting mixture was heated
  3. temperatureto reflux for 1.5 hours
  4. temperaturecooled until precipitate
  5. customwas formed
  6. filtrationThe solid was filtered
  7. washwashed with water (50 ml×3)
  8. customdried in vacuo

Sources & evidence

ORD record
ord-bd39b971f32e48b8a4a2c7984f460e60
Source dataset
uspto-grants-2013_01
Patent number
US08362251B2

Reaction notes

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