Pyrrolidine → 3-bromo-1-(4-methoxy-benzyl)-5-pyrrolidin-1-yl-1H-[1,2,4]triazole

HRID 1054945Notes

Reaction equation

HRID 1054945 reaction equation
[Br:1][C:2]1[N:6]=[C:5](Br)[N:4]([CH2:8][C:9]2[CH:14]=[CH:13][C:12]([O:15][CH3:16])=[CH:11][CH:10]=2)[N:3]=1.[NH:17]1[CH2:21][CH2:20][CH2:19][CH2:18]1>CN(C)C=O>[Br:1][C:2]1[N:6]=[C:5]([N:17]2[CH2:21][CH2:20][CH2:19][CH2:18]2)[N:4]([CH2:8][C:9]2[CH:14]=[CH:13][C:12]([O:15][CH3:16])=[CH:11][CH:10]=2)[N:3]=1

Participants

4

Reactant 2

HCID 31268PyrrolidineHCID 179319143,5-dibromo-1-(4-methoxybenzyl)-1H-1,2,4-triazole

Product 1

HCID 900169503-bromo-1-(4-methoxy-benzyl)-5-pyrrolidin-1-yl-1H-[1,2,4]triazoleYield 49.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 3,5-dibromo-1-(4-methoxybenzyl)-1H-1,2,4-triazole (1.268 g, 3.65 mmol, Eq: 1.00) and pyrrolidine (273 mg, 317 μl, 3.84 mmol, Eq: 1.05) in dimethyl formamide (12 ml) was heated for 18 hours to 110° C. under argon atmosphere. The crude material was applied on silicagel and purified by flash chromatography over a 50 g silicagel column using heptane/ethyl acetate 30-50% as eluent affording 3-bromo-1-(4-methoxy-benzyl)-5-pyrrolidin-1-yl-1H-[1,2,4]triazole (608 mg/49.3%) as a colorless oil. MS: m/e=338339 (M+H+)

Workup

  1. temperaturewas heated for 18 hours to 110° C. under argon atmosphere
  2. custompurified by flash chromatography over a 50 g silicagel column

Sources & evidence

ORD record
ord-1c49109ae1a54467b2bc3e7c1b75b2f0
Source dataset
uspto-grants-2016_07
Patent number
US09394311B2

Reaction notes

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