4-Toluenesulfonyl chloride → 5-(3-iodo-1-tosyl-1H-indol-5-yl)-N-(4-methoxybenzyl)-1,3,4-oxadiazol-2-amine

HRID 634090Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 634090
[I:1][C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([C:11]3[O:15][C:14]([NH:16][CH2:17][C:18]4[CH:23]=[CH:22][C:21]([O:24][CH3:25])=[CH:20][CH:19]=4)=[N:13][N:12]=3)[CH:9]=2)[NH:4][CH:3]=1.[H-].[Na+].[CH3:28][C:29]1[CH:34]=[CH:33][C:32]([S:35](Cl)(=[O:37])=[O:36])=[CH:31][CH:30]=1>CN(C=O)C>[I:1][C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([C:11]3[O:15][C:14]([NH:16][CH2:17][C:18]4[CH:23]=[CH:22][C:21]([O:24][CH3:25])=[CH:20][CH:19]=4)=[N:13][N:12]=3)[CH:9]=2)[N:4]([S:35]([C:32]2[CH:33]=[CH:34][C:29]([CH3:28])=[CH:30][CH:31]=2)(=[O:37])=[O:36])[CH:3]=1

Komponenten

5

Edukt 3

HCID 73974-Toluenesulfonyl chlorideHCID 24758Sodium hydrideHCID 867250895-(3-iodo-1H-indol-5-yl)-N-(4-methoxybenzyl)-1,3,4-oxadiazol-2-amine

Produkt 1

HCID 683283255-(3-iodo-1-tosyl-1H-indol-5-yl)-N-(4-methoxybenzyl)-1,3,4-oxadiazol-2-amineAusbeute 67 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel2×

Reaktionsbedingungen

Temperatur
-25 °C

Versuchsvorschrift

To a solution of 5-(3-iodo-1H-indol-5-yl)-N-(4-methoxybenzyl)-1,3,4-oxadiazol-2-amine (0.5 g, 1.12 mmol) in DMF (5 mL) at −25° C. was added NaH (0.059 g, 50% in mineral oil, 1.23 mmol) portion wise. The mixture was stirred for 5 min at −25° C. then a solution of 4-methyl benzene sulfonyl chloride (0.235 g, 1.23 mmol) in DMF (1 mL) was added at same temperature dropwise. The reaction was stirred at −25° C. for 10 min. The mixture was poured into ice cold water and a white solid precipitated out which was collected by filtration and recrystallized by triturating it with 1:3 volume of EtOH (2 mL) and CHCl3 (6 mL) to give 5-(3-iodo-1-tosyl-1H-indol-5-yl)-N-(4-methoxybenzyl)-1,3,4-oxadiazol-2-amine (0.450 g, 0.75 mmol, 66.96%). MS (ESI, pos. ion) m/z: 601.1 (M+1); 1H-NMR (DMSO-d6) δ8.312 (s, 1H), 8.21 (s, 1H), 8.13 (s, 1H), 7.9-7.90 (m, 3H), 7.68 (s, 1H), 7.44 (d, J=9 Hz, 2H), 7.33 (d, J=9 Hz, 2H), 6.92 (d, J=9 Hz, 2H), 4.38 (d, J=6 Hz, 2H), 3.73 (s, 3H), 2.33 (s, 3H).

Aufarbeitung

  1. stirringThe reaction was stirred at −25° C. for 10 min
  2. additionThe mixture was poured into ice cold water
  3. customa white solid precipitated out which
  4. filtrationwas collected by filtration
  5. customrecrystallized
  6. customby triturating it with 1:3 volume of EtOH (2 mL) and CHCl3 (6 mL)

Quellen und Nachweise

ORD-Eintrag
ord-340c98c944a749ef95d1abec246e58df
Quelldatensatz
uspto-grants-2016_04
Patentnummer
US09321756B2

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