Pyrrolidine → 7-Bromo-2-(pyrrolidin-1-yl)-[1,2,4]triazolo[1,5-a]pyridine

HRID 1802236Notes

Reaction equation

HRID 1802236 reaction equation
Br[C:2]1[N:11]=[C:5]2[CH:6]=[C:7]([Br:10])[CH:8]=[CH:9][N:4]2[N:3]=1.[NH:12]1[CH2:16][CH2:15][CH2:14][CH2:13]1>>[Br:10][C:7]1[CH:8]=[CH:9][N:4]2[N:3]=[C:2]([N:12]3[CH2:16][CH2:15][CH2:14][CH2:13]3)[N:11]=[C:5]2[CH:6]=1

Participants

3

Reactant 2

HCID 31268PyrrolidineHCID 677742742,7-Dibromo[1,2,4]triazolo[1,5-a]pyridine

Product 1

HCID 677758077-Bromo-2-(pyrrolidin-1-yl)-[1,2,4]triazolo[1,5-a]pyridineYield 51.6%

Procedure

A mixture of 2,7-dibromo-[1,2,4]triazolo[1,5-a]pyridine (770 mg, 2.78 mmol) and pyrrolidine (15 ml, 181 mmol) was refluxed for 3 hours under nitrogen atmosphere. The pyrrolidine was evaporated. The residue was diluted with ethyl acetate and washed with water and brine. The organic layer was separated, dried over magnesium sulfate, filtrated and evaporated. The crude material was applied on silicagel and purified by flash chromatography over a 50 g silicagel column using heptane/ethyl acetate 10-50% as eluent affording 7-bromo-2-pyrrolidin-1-yl-[1,2,4]triazolo[1,5-a]pyridine (383 mg, 51.5%) as an off-white solid. mp: 170-172° C., MS: m/z=266.9/269 (M+H+)

Workup

  1. temperaturewas refluxed for 3 hours under nitrogen atmosphere
  2. customThe pyrrolidine was evaporated
  3. additionThe residue was diluted with ethyl acetate
  4. washwashed with water and brine
  5. customThe organic layer was separated
  6. dry with materialdried over magnesium sulfate
  7. filtrationfiltrated
  8. customevaporated
  9. custompurified by flash chromatography over a 50 g silicagel column

Sources & evidence

ORD record
ord-2dfddc88253e44f7aeccc858156b2d63
Source dataset
uspto-grants-2013_01
Patent number
US08349824B2

Reaction notes

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