Water → HCID 21914123, compound

HRID 887919Notes

Reaction equation

HRID 887919 reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][CH:6]([C:11]([NH2:13])=[O:12])[CH2:5]2.C(N(CC)CC)C.[C:21](Cl)(=[O:23])[CH3:22].O>C(Cl)Cl>[C:21]([N:7]1[C:8]2[C:4](=[CH:3][C:2]([F:1])=[CH:10][CH:9]=2)[CH2:5][CH:6]1[C:11]([NH2:13])=[O:12])(=[O:23])[CH3:22]

Participants

6

Reactant 4

HCID 962WaterHCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 21914120HCID 21914120, compound

Product 1

HCID 21914123HCID 21914123, compoundYield 75.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a mixture of intermediate (17) (0.0094 mole) in DCM (30 ml), cooled in an ice bath under argon, was added triethylamine (0.031 mole) followed by acetyl chloride (0.031 mole). The resulting mixture was allowed to return to room temperature. After stiffing for 6 hours, the mixture was cooled in an ice bath and 50 ml of water was added. The mixture was allowed to stir about 20 minutes, was filtered and the solid was allowed to dry to obtain 1.58 g of 1-acetyl-5-fluoro-2,3-dihydro-1H-indole-2-carboxamide (intermediate 18, mp. 232-235° C.).

Workup

  1. temperaturecooled in an ice bath under argon
  2. customto return to room temperature
  3. temperaturethe mixture was cooled in an ice bath
  4. filtrationwas filtered
  5. customto dry

Sources & evidence

ORD record
ord-18bc32025cc24931aedc0f8c9613798c
Source dataset
uspto-grants-2012_08
Patent number
US08247432B2

Reaction notes

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