1,1'-Carbonyldiimidazole → 5-(3-iodo-1-tosyl-1H-indol-5-yl)-1,3,4-oxadiazol-2(3H)-one

HRID 634194Notes

Reaction equation

HRID 634194 reaction equation
[I:1][C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([C:11]([NH:13][NH2:14])=[O:12])[CH:9]=2)[N:4]([S:15]([C:18]2[CH:24]=[CH:23][C:21]([CH3:22])=[CH:20][CH:19]=2)(=[O:17])=[O:16])[CH:3]=1.C(N(C(C)C)C(C)C)C.C1N=CN([C:39](N2C=NC=C2)=[O:40])C=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:12][C:39](=[O:40])[NH:14][N:13]=3)[CH:9]=2)[N:4]([S:15]([C:18]2[CH:24]=[CH:23][C:21]([CH3:22])=[CH:20][CH:19]=2)(=[O:16])=[O:17])[CH:3]=1

Participants

5

Reactant 3

HCID 682631,1'-CarbonyldiimidazoleHCID 81531DiisopropylethylamineHCID 683285283-iodo-1-tosyl-1H-indole-5-carbohydrazide

Product 1

HCID 683283805-(3-iodo-1-tosyl-1H-indol-5-yl)-1,3,4-oxadiazol-2(3H)-oneYield 80.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 3-iodo-1-tosyl-1H-indole-5-carbohydrazide (2.00 g, 4.39 mmol) in DMF (10 mL) at RT was added N-ethyl-N-isopropylpropan-2-amine (1.68 mL, 9.66 mmol) and CDI (0.784 g, 4.83 mmol). The reaction was stirred at RT for 30 min, followed by 65° C. in an oil bath for 15 min. It was concentrated under reduced pressure and the residue was purified by flash chromatography on silica gel (eluted with 20-70% EtOAc in Hex) to afford 5-(3-iodo-1-tosyl-1H-indol-5-yl)-1,3,4-oxadiazol-2(3H)-one (1.7 g, 80%) as an off white crystalline solid. MS (ESI, pos. ion) m/z: 482.0 (M+1).

Workup

  1. waitfollowed by 65° C. in an oil bath for 15 min
  2. concentrationIt was concentrated under reduced pressure
  3. customthe residue was purified by flash chromatography on silica gel (eluted with 20-70% EtOAc in Hex)

Sources & evidence

ORD record
ord-d0148befdb5c43a89fb01ecec5a659b9
Source dataset
uspto-grants-2016_04
Patent number
US09321756B2

Reaction notes

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