Methanol → HCID 84046085, compound

HRID 1482913Notes

Reaction equation

HRID 1482913 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([N:8]2[CH:12]=[C:11]([C:13]([O:15]C)=[O:14])[N:10]=[N:9]2)=[N:6][CH:7]=1.CO.O>O1CCCC1>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([N:8]2[CH:12]=[C:11]([C:13]([OH:15])=[O:14])[N:10]=[N:9]2)=[N:6][CH:7]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 962WaterHCID 90047243HCID 90047243, compound

Product 1

HCID 84046085HCID 84046085, compoundYield 98%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
70 °C

Procedure

To a solution of methyl 1-(5-bromopyridin-2-yl)-1H-1,2,3-triazole-4-carboxylate (240 mg, 0.85 mmol) in a mixture of tetrahydrofuran (2.4 ml), methanol (2.4 ml) and water (2.4 ml) lithium hydroxide hydrate (107 mg, 2.54 mmol) was added. The solution was heated to 70° C. for 3 h. Most of the organic solvent was removed under reduced pressure. Water was added and the solution was extracted once with ether. Then 4 N hydrochloric acid was added to reach acidic pH. The product precipitated and the mixture was extracted three times with ethyl acetate. The organic layers were combined, dried (MgSO4) and evaporated to yield a light brown solid (223 mg, 98%). MS (ISP): 269.4 ({79Br} [M+H]+), 271.4 ({81Br} [M+H]+).

Workup

  1. additionwas added
  2. customMost of the organic solvent was removed under reduced pressure
  3. additionWater was added
  4. extractionthe solution was extracted once with ether
  5. additionThen 4 N hydrochloric acid was added
  6. customThe product precipitated
  7. extractionthe mixture was extracted three times with ethyl acetate
  8. dry with materialdried (MgSO4)
  9. customevaporated

Sources & evidence

ORD record
ord-503a501cb76d4dfaa3a45378af918fdd
Source dataset
uspto-grants-2016_08
Patent number
US09416127B2

Reaction notes

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