Morpholine → 4-(6-Bromo-[1,2,4]triazolo[1,5-A]pyridin-2-YL)morpholine

HRID 1844449Notes

Reaction equation

HRID 1844449 reaction equation
Br[C:2]1[N:11]=[C:5]2[CH:6]=[CH:7][C:8]([Br:10])=[CH:9][N:4]2[N:3]=1.[NH:12]1[CH2:17][CH2:16][O:15][CH2:14][CH2:13]1>>[Br:10][C:8]1[CH:7]=[CH:6][C:5]2[N:4]([N:3]=[C:2]([N:12]3[CH2:17][CH2:16][O:15][CH2:14][CH2:13]3)[N:11]=2)[CH:9]=1

Participants

3

Reactant 2

HCID 8083MorpholineHCID 683908752,6-Dibromo-[1,2,4]triazolo[1,5-a]pyridine

Product 1

HCID 717438774-(6-Bromo-[1,2,4]triazolo[1,5-A]pyridin-2-YL)morpholineYield 66%

Procedure

A mixture of 2,6-dibromo-[1,2,4]triazolo[1,5-a]pyridine (1 g, 3.61 mmol) and morpholine (10 g, 10 ml, 115 mmol) was refluxed for 4 hours under argon atmosphere. The mixture was evaporated to dryness under reduced pressure. Flash chromatography (silica gel, 50 g, 30-100% heptane/ethyl acetate) afforded 6-bromo-2-morpholin-4-yl-[1,2,4]triazolo[1,5-a]pyridine (672 mg, 66%) as a light yellow solid. Mp.: 136° C. MS: m/z=283.0/285.0 (M+H+).

Workup

  1. temperaturewas refluxed for 4 hours under argon atmosphere
  2. customThe mixture was evaporated to dryness under reduced pressure

Sources & evidence

ORD record
ord-50268b3f864d47d9a8e1324dc090e31a
Source dataset
uspto-grants-2015_02
Patent number
US08946427B2

Reaction notes

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