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

HRID 905723Notes

Reaction equation

HRID 905723 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(N(CC)CC)C.[C:39](Cl)(=[O:41])[CH3:40]>O1CCCC1>[F:31][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][C:2]=1[NH:1][C:39](=[O:41])[CH3:40])[NH:8][C:7](=[O:11])[CH2:6]2

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 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 triethylamine (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-c227ea8be2da4d62be64e61e9d0a28b7
Source dataset
uspto-grants-2011_09
Patent number
US08012966B2

Reaction notes

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