Dimethylformamide → tert-butyl 3-iodo-5-(5-(methylthio)-1,3,4-thiadiazol-2-yl)-1H-indole-1-carboxylate

HRID 634122Notes

Reaction equation

HRID 634122 reaction equation
[I:1][C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([C:11]3[S:12][C:13]([S:16][CH3:17])=[N:14][N:15]=3)[CH:9]=2)[NH:4][CH:3]=1.[CH3:18][C:19]([CH3:22])([O-:21])[CH3:20].[K+].CN([CH:27]=[O:28])C>>[I:1][C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([C:11]3[S:12][C:13]([S:16][CH3:17])=[N:14][N:15]=3)[CH:9]=2)[N:4]([C:27]([O:21][C:19]([CH3:22])([CH3:20])[CH3:18])=[O:28])[CH:3]=1

Participants

4

Reactant 3

HCID 6228DimethylformamideHCID 23665647Potassium tert-butoxideHCID 683283122-(3-iodo-1H-indol-5-yl)-5-(methylthio)-1,3,4-thiadiazole

Product 1

HCID 68328746tert-butyl 3-iodo-5-(5-(methylthio)-1,3,4-thiadiazol-2-yl)-1H-indole-1-carboxylateYield 75%

Procedure

To a solution of 2-(3-iodo-1H-indol-5-yl)-5-(methylthio)-1,3,4-thiadiazole (21 g, 56.3 mmol) in DMF (210 mL) was added potassium tert-butoxide (12.6 g, 112.6 mol) and followed by di-tert-butyl-di-cabonate (24.5 g, 112.6 mmol). The reaction was stirred at RT for 2 h, and ice/H2O was added. The resulting precipitate was filtered and washed with H2O to give tert-butyl 3-iodo-5-(5-(methylthio)-1,3,4-thiadiazol-2-yl)-1H-indole-1-carboxylate (20 g, 75%). MS (ESI, pos. ion) m/z: 473.8 (M+1). 1HNMR (DMSO-d6, 300 MHz): δ 2.8 (s, 3H), 7.5 (d, 1H), 7.7 (m, 2H), 12.0 (s, 1H).

Workup

  1. filtrationThe resulting precipitate was filtered
  2. washwashed with H2O

Sources & evidence

ORD record
ord-26c927d11aba4b0abc0dbde6d4093150
Source dataset
uspto-grants-2016_04
Patent number
US09321756B2

Reaction notes

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