Water → HCID 90047243, compound

HRID 1482912Notes

Reaction equation

HRID 1482912 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([N:8]=[N:9][N:10]=2)[CH:7]=1.[C:11]([O:15][CH3:16])(=[O:14])[C:12]#[CH:13].N1C(C)=CC=CC=1C.O>O1CCCC1.CS(C)=O.[Cu]I>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([N:10]2[CH:13]=[C:12]([C:11]([O:15][CH3:16])=[O:14])[N:8]=[N:9]2)=[N:6][CH:7]=1

Participants

8

Reactant 4

HCID 962WaterHCID 79372,6-LutidineHCID 13536Methyl propiolateHCID 216259586-Bromotetrazolo[1,5-a]pyridine

Product 1

HCID 90047243HCID 90047243, compoundYield 100.9%

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 679Dimethyl SulfoxideSolventHCID 8028TetrahydrofuranSolvent

Procedure

In a 10 ml round-bottomed flask, 6-bromotetrazolo[1,5-a]pyridine (209 mg, 1.05 mmol) was dissolved in a mixture of tetrahydrofuran (3.5 ml) and dimethylsulfoxide (0.06 ml) to give an orange solution. Methyl propiolate (265 mg, 276 μl, 3.15 mmol), copper (I) iodide (200 mg, 1.05 mmol) and 2,6-lutidine (225 mg, 245 μl, 2.1 mmol) were added and the reaction mixture was stirred at room temperature overnight. Water was added and the layers were separated using ethyl acetate. The organic layer was washed with 1 N hydrochloric acid and brine, dried over magnesium sulphate and filtered. The filtrate was concentrated under vacuum to yield a brown solid (300 mg), which was adsorbed on silica gel. Purification by flash chromatography (Silica gel, 20 g, 10 to 30% EtOAc in heptane) yielded a light grey solid (255 mg, 86%). MS (ISP): 283.4 ({79Br} [M+H]+), 285.4 ({81Br} [M+H]+).

Workup

  1. customto give an orange solution
  2. customthe layers were separated
  3. washThe organic layer was washed with 1 N hydrochloric acid and brine
  4. dry with materialdried over magnesium sulphate
  5. filtrationfiltered
  6. concentrationThe filtrate was concentrated under vacuum

Sources & evidence

ORD record
ord-d3367a9031a646a289c738efeb044e1b
Source dataset
uspto-grants-2016_08
Patent number
US09416127B2

Reaction notes

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