Pyridine → HCID 84671998, compound

HRID 1055023Notes

Reaction equation

HRID 1055023 reaction equation
[Br:1][C:2]1[N:6]=[C:5]([CH:7]([OH:9])[CH3:8])[N:4]([CH3:10])[N:3]=1.N1C=CC=CC=1.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O>ClCCl>[Br:1][C:2]1[N:6]=[C:5]([C:7](=[O:9])[CH3:8])[N:4]([CH3:10])[N:3]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 159087TriacetoxyperiodinaneHCID 900176691-(3-Bromo-1-methyl-1H-1,2,4-triazol-5-YL)ethan-1-OL

Product 1

HCID 84671998HCID 84671998, compoundYield 58.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

A solution of 1-(3-bromo-1-methyl-1H-1,2,4-triazol-5-yl)ethanol (1.639 g, 7.95 mmol, Eq: 1.00) and pyridine (944 mg, 965 μl, 11.9 mmol, Eq: 1.5) in dichloromethane (237 ml) was cooled to 0° C. then Dess-Martin periodinane (15% in dichloromethane, 24.7 g, 8.75 mmol, Eq: 1.1) was added. The resulting mixture was stirred for 4 hours at 0° C. under nitrogen atmosphere. The mixture was diluted with dichloromethane and washed with sat. sodium hydrogen carbonate. The organic layer was separated, dried over magnesium sulfate, filtrated and evaporated. The crude material was applied on silica gel and purified by flash chromatography over a 20 g silica gel column using dichloromethane/methanol 0-3% & 5% NH3 as eluent affording 1-(5-bromo-2-methyl-2H-[1,2,4]triazol-3-yl)-ethanone (948 mg, 58.4%) as a white solid. MS: m/z=203 (EI)

Workup

  1. washwashed with sat. sodium hydrogen carbonate
  2. customThe organic layer was separated
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltrated
  5. customevaporated
  6. custompurified by flash chromatography over a 20 g silica gel column

Sources & evidence

ORD record
ord-0d9657c11442411ab611afac4dc96f33
Source dataset
uspto-grants-2016_07
Patent number
US09394311B2

Reaction notes

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