Potassium Carbonate → 7-Fluoro-1-(2-fluoroethyl)indoline-2,3-dione

HRID 2114884Notes

Reaction equation

HRID 2114884 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:10]=1[NH:9][C:8](=[O:11])[C:7]2=[O:12].I[CH2:14][CH2:15][F:16].C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C.O>[F:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:10]=1[N:9]([CH2:14][CH2:15][F:16])[C:8](=[O:11])[C:7]2=[O:12]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 69804Ethane, 1-fluoro-2-iodo-HCID 5864187-Fluoroisatin

Product 1

HCID 739475787-Fluoro-1-(2-fluoroethyl)indoline-2,3-dione

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

7-Fluoro-1H-indole-2,3-dione (prepared according to the method of Gassman as described in U.S. Pat. No. 4,188,325 (2.00 g, 12.1 mmol), 1-iodo-2-fluoroethane (4.21 g, 24.2 mmol) and potassium carbonate (3.30 g, 24.2 mmol) in DMF (20 ml) are stirred at room temperature for 20 hours. The reaction mixture is diluted with cold water and the resulting precipitate filtered and dried to give the title compound as an orange solid. HPLC r.t. 4.18 min; MS for C10H7F2NO2 m/z 212.1 (M+H)+.

Workup

  1. filtrationthe resulting precipitate filtered
  2. customdried

Sources & evidence

ORD record
ord-7494a463e40545238fc5aa7c3d99a983
Source dataset
uspto-grants-2008_10
Patent number
US07435751B2

Reaction notes

Loading…