5,6-difluoro-2,3-dihydro-1H-indole-2,3-dione → 6-Ethylthio-5-fluoroindole-2,3-dione
Reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][C:10]=1F)[NH:7][C:6](=[O:12])[C:5]2=[O:13].[S-:14][CH2:15][CH3:16].[Na+].FC1C=C2C(=CC=1SC)NC=C2>>[CH2:15]([S:14][C:10]1[CH:9]=[C:8]2[C:4]([C:5](=[O:13])[C:6](=[O:12])[NH:7]2)=[CH:3][C:2]=1[F:1])[CH3:16]Participants
4
Procedure
6-Ethylthio-5-fluoroindole-2,3-dione was prepared from 5,6-difluoroindole-2,3-dione using sodium thioethoxide according to the method described in the synthesis of 5-fluoro-6-methylthioindole as a brown solid (2.53 g, 19%): mp 215° C.; IR νmax (Nujol)/cm−1 3286, 2926, 2855, 1766, 1712, 1619, 1467 and 1038; NMR δH (400 MHz, DMSO-d6) 1.32 (3H, t, J 7.5 Hz), 3.13 (2H, q, J 7.5 Hz), 6.77 (1H, d, J 6.0 Hz), 7.39 (1H, d, J 8.5 Hz), 10.97 (1H, brs).
Sources & evidence
- ORD record
- ord-5cc7f360b26549b1a83fb3dff871ef3d
- Source dataset
- uspto-grants-2002_04
- Patent number
- US06380238B1
Reaction notes
Loading…