Methyl iodide → HCID 57837442, compound

HRID 731730Notes

Reaction equation

HRID 731730 reaction equation
[OH:1][CH:2]([CH3:17])[C:3]([C:5]1[C:6]([CH:14]([CH3:16])[CH3:15])=[N:7][N:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=12)=[O:4].[CH3:18]I>C1COCC1.[Ag]=O>[CH:14]([C:6]1[C:5]([C:3](=[O:4])[CH:2]([O:1][CH3:18])[CH3:17])=[C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][N:8]2[N:7]=1)([CH3:16])[CH3:15]

Participants

5

Reactant 2

HCID 6328Methyl iodideHCID 57837502HCID 57837502, compound

Product 1

HCID 57837442HCID 57837442, compound

Reagents, catalysts & solvents 2

HCID 92152Silver(II) oxideCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 2-hydroxy-1-(2-isopropylpyrazolo[1,5-a]pyridin-3-yl)propan-1-one (0.6 g, 1 equivalent), silver oxide (5 g, 8 equivalents), and methyl iodide (2.5 mL, 15 equivalents) in 2 mL of THF was stirred in a sealed tube at room temperature for 26 hours. The mixture was filtered to remove precipitated solids. The filtrate was worked up with ethyl acetate and saturated NaHCO3. The crude oil obtained was purified by silica gel flash column chromatography to give 1-(2-isopropylpyrazolo[1,5-a]pyridin-3-yl)-2-methoxypropan-1-one as an oil. Compound 1069.

Workup

  1. filtrationThe mixture was filtered
  2. customto remove
  3. customprecipitated solids
  4. customThe crude oil obtained
  5. customwas purified by silica gel flash column chromatography

Sources & evidence

ORD record
ord-d6a46ce93dc04dffbed511c683b5ea5a
Source dataset
uspto-grants-2009_09
Patent number
US07585875B2

Reaction notes

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