Potassium Iodide → 2-(4-Iodophenyl)-5-pyrrolidin-1-ylmethyl-[1,3,4]oxadiazole

HRID 31404

Reaction equation

HRID 31404 reaction equation
Cl[CH2:2][C:3]1[O:4][C:5]([C:8]2[CH:13]=[CH:12][C:11]([I:14])=[CH:10][CH:9]=2)=[N:6][N:7]=1.[I-].[K+].[NH:17]1[CH2:21][CH2:20][CH2:19][CH2:18]1>>[I:14][C:11]1[CH:12]=[CH:13][C:8]([C:5]2[O:4][C:3]([CH2:2][N:17]3[CH2:21][CH2:20][CH2:19][CH2:18]3)=[N:7][N:6]=2)=[CH:9][CH:10]=1

Participants

4

Reactant 3

HCID 4875Potassium IodideHCID 31268PyrrolidineHCID 70910682-(Chloromethyl)-5-(4-iodophenyl)-1,3,4-oxadiazole2×

Product 1

HCID 693160992-(4-Iodophenyl)-5-pyrrolidin-1-ylmethyl-[1,3,4]oxadiazole

Conditions

Temperature
20 °C

Procedure

2-Chloromethyl-5-(4-iodophenyl)-[1,3,4]oxadiazole (Intermediate 7) (48 mg, 0.15 mmol) and potassium iodide (25 mg, 0.15 mmol) were dissolved in pyrrolidine (2 ml) and stirred for 18 hours at 20° C. The amine was then removed in vacuo and the product was purified on a 10 g silica SPE cartridge (stepped solvent gradient 80:20 ethyl acetate:cyclohexane, 100% ethyl acetate, 95:5 ethyl acetate:methanol).

Workup

  1. customThe amine was then removed in vacuo
  2. customthe product was purified on a 10 g silica SPE cartridge (stepped solvent gradient 80:20 ethyl acetate:cyclohexane, 100% ethyl acetate, 95:5 ethyl acetate:methanol)

Sources & evidence

ORD record
ord-915b3342c89b473bb544c6193c6b64d0
Source dataset
uspto-grants-2008_09
Patent number
US07425555B2

Linked notes

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