Acetic Acid → tert-butyl 5-(5-(methylsulfonyl)-1,3,4-thiadiazol-2-yl)-3-(quinolin-3-yl)-1H-indole-1-carboxylate

HRID 634150Notes

Reaction equation

HRID 634150 reaction equation
[CH3:1][S:2][C:3]1[S:7][C:6]([C:8]2[CH:9]=[C:10]3[C:14](=[CH:15][CH:16]=2)[N:13]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH:12]=[C:11]3[C:24]2[CH:25]=[N:26][C:27]3[C:32]([CH:33]=2)=[CH:31][CH:30]=[CH:29][CH:28]=3)=[N:5][N:4]=1.CC(O)=[O:36].OO.[OH2:40]>>[CH3:1][S:2]([C:3]1[S:7][C:6]([C:8]2[CH:9]=[C:10]3[C:14](=[CH:15][CH:16]=2)[N:13]([C:17]([O:19][C:20]([CH3:23])([CH3:21])[CH3:22])=[O:18])[CH:12]=[C:11]3[C:24]2[CH:25]=[N:26][C:27]3[C:32]([CH:33]=2)=[CH:31][CH:30]=[CH:29][CH:28]=3)=[N:5][N:4]=1)(=[O:36])=[O:40]

Participants

5

Reactant 4

HCID 176Acetic AcidHCID 784Hydrogen PeroxideHCID 962Water2×HCID 68328445tert-butyl 5-(5-(methylthio)-1,3,4-thiadiazol-2-yl)-3-(quinolin-3-yl)-1H-indole-1-carboxylate

Product 1

HCID 68328257tert-butyl 5-(5-(methylsulfonyl)-1,3,4-thiadiazol-2-yl)-3-(quinolin-3-yl)-1H-indole-1-carboxylateYield 94%

Procedure

To a stirred solution of tert-butyl 5-(5-(methylthio)-1,3,4-thiadiazol-2-yl)-3-(quinolin-3-yl)-1H-indole-1-carboxylate (38 mg, 80 μmol) in glacial HOAc (0.5 mL, 8659 μmol) with catalytic amount of NaWO4 (0.0003 mL, 4 μmol) was added dropwise H2O2, 35 wt. % solution in H2O (0.01 mL, 323 μmol) and the overall yellow mixture was stirred at RT for 1.5 h. The cloudy mixture was diluted with H2O and the resulting precipitate was filtered, washed with H2O and dried in vacuo to give tert-butyl 5-(5-(methylsulfonyl)-1,3,4-thiadiazol-2-yl)-3-(quinolin-3-yl)-1H-indole-1-carboxylate (38 mg, 94%) as a yellow solid. MS (ESI, pos. ion) m/z: 507 (M+1).

Workup

  1. filtrationthe resulting precipitate was filtered
  2. washwashed with H2O
  3. customdried in vacuo

Sources & evidence

ORD record
ord-09991d0ee3de4c02902ba3176ca0f108
Source dataset
uspto-grants-2016_04
Patent number
US09321756B2

Reaction notes

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