5-(3-(6-fluoropyridin-2-yl)-1-tosyl-1H-indol-5-yl)-N-(4-methoxybenzyl)-1,3,4-thiadiazol-2-amine → 5-(3-(6-fluoropyridin-2-yl)-1-tosyl-1H-indol-5-yl)-1,3,4-thiadiazol-2-amine
Reaktionsgleichung
[F:1][C:2]1[N:7]=[C:6]([C:8]2[C:16]3[C:11](=[CH:12][CH:13]=[C:14]([C:17]4[S:21][C:20]([NH:22]CC5C=CC(OC)=CC=5)=[N:19][N:18]=4)[CH:15]=3)[N:10]([S:32]([C:35]3[CH:41]=[CH:40][C:38]([CH3:39])=[CH:37][CH:36]=3)(=[O:34])=[O:33])[CH:9]=2)[CH:5]=[CH:4][CH:3]=1>C(O)(C(F)(F)F)=O>[F:1][C:2]1[N:7]=[C:6]([C:8]2[C:16]3[C:11](=[CH:12][CH:13]=[C:14]([C:17]4[S:21][C:20]([NH2:22])=[N:19][N:18]=4)[CH:15]=3)[N:10]([S:32]([C:35]3[CH:36]=[CH:37][C:38]([CH3:39])=[CH:40][CH:41]=3)(=[O:34])=[O:33])[CH:9]=2)[CH:5]=[CH:4][CH:3]=1Komponenten
3
Edukt 1
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Reaktionsbedingungen
- Temperatur
- 120 °C
Versuchsvorschrift
A glass microwave reaction vessel was charged with 5-(3-(6-fluoropyridin-2-yl)-1-tosyl-1H-indol-5-yl)-N-(4-methoxybenzyl)-1,3,4-thiadiazol-2-amine (400 mg, 0.683 mmol) in TFA (0.5 mL). The reaction was stirred and heated in a Initiator microwave reactor (Personal Chemistry, Biotage AB, Inc., Uppsala, Sweden) at 120° C. for 30 min. The solvent was removed and the residue was diluted with DCM and washed with sat. NaHCO3. The organic layer was dried, filtered and concentrated. The residue was purified with silica gel chromatography (eluting with 10-25% EtOAc in DCM with 1% MeOH) to give 5-(3-(6-fluoropyridin-2-yl)-1-tosyl-1H-indol-5-yl)-1,3,4-thiadiazol-2-amine (250 mg, 0.537 mmol, 79%) as a white solid. MS (ESI, pos. ion) m/z: 466 (M+1).