Morpholine → 7-Bromo-2-(4-morpholinyl)[1,2,4]triazolo[1,5-a]pyridine

HRID 1802148Notes

Reaction equation

HRID 1802148 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[CH2:17][CH2:16][O: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[CH2:17][CH2:16][O:15][CH2:14][CH2:13]3)[N:11]=[C:5]2[CH:6]=1

Participants

3

Reactant 2

HCID 8083MorpholineHCID 677742742,7-Dibromo[1,2,4]triazolo[1,5-a]pyridine

Product 1

HCID 677768607-Bromo-2-(4-morpholinyl)[1,2,4]triazolo[1,5-a]pyridineYield 35.9%

Procedure

A mixture of 2,7-dibromo-[1,2,4]triazolo[1,5-a]pyridine (1 g, 3.61 mmol) and morpholine (10.0 g, 10 ml, 115 mmol) was refluxed for 4 hours under argon atmosphere, the formerly green mixture turning to yellow. The reaction mixture is concentrated to dryness, applied on silica and purified by flash chromatography on a 20 g silica column using heptane/ethyl acetate 10-100% as eluent affording 4-(7-bromo-[1,2,4]triazolo[1,5-a]pyridin-2-yl)morpholine (367 mg, 35.9%) as a white solid. mp.: 178-9° C. MS: m/z=285.0, 283.0 (M+H+).

Workup

  1. temperaturewas refluxed for 4 hours under argon atmosphere
  2. concentrationThe reaction mixture is concentrated to dryness
  3. custompurified by flash chromatography on a 20 g silica column

Sources & evidence

ORD record
ord-e16158c742354862a05a91aaa07942e4
Source dataset
uspto-grants-2013_01
Patent number
US08349824B2

Reaction notes

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