Ethylene Glycol → HCID 25181650, compound

HRID 1896024Notes

Reaction equation

HRID 1896024 reaction equation
[O-]P([O-])([O-])=O.[K+].[K+].[K+].C(O)CO.I[C:14]1[C:15]([O:20][CH2:21][CH2:22][CH3:23])=[N:16][CH:17]=[CH:18][CH:19]=1.[CH3:24][C:25]1[CH:30]=[CH:29][CH:28]=[C:27]([C:31]#[C:32][CH:33]=[C:34]2[CH2:39][CH2:38][NH:37][CH2:36][CH2:35]2)[N:26]=1>C(O)CCC.CCOC(C)=O.[Cu]I>[CH3:24][C:25]1[CH:30]=[CH:29][CH:28]=[C:27]([C:31]#[C:32][CH:33]=[C:34]2[CH2:35][CH2:36][N:37]([C:14]3[C:15]([O:20][CH2:21][CH2:22][CH3:23])=[N:16][CH:17]=[CH:18][CH:19]=3)[CH2:38][CH2:39]2)[N:26]=1

Participants

8

Reactant 4

HCID 174Ethylene GlycolHCID 62657Potassium Phosphate, TribasicHCID 425531323-Iodo-2-propoxypyridineHCID 875504022-Methyl-6-(3-piperidin-4-ylideneprop-1-ynyl)pyridine

Product 1

HCID 25181650HCID 25181650, compoundYield 10%

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 2631-ButanolSolvent2×HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
100 °C

Procedure

Into a flamed flask flushed with nitrogen a mixture of CuI (19.4 mg. 0.1 mmol)), K3PO4 (425 mg, 2 mmol), ethylene glycol (112 μL), 3-iodo-2-propoxypyridine (263 mg, 1 mmol) in 1 mL of n-Butanol were added 255 mg of the compound of Example 3 dissolved in 1 mL of n-Butanol. The suspension was heated at 100° C. for 5 h. The reaction mixture was then cooled to r.t., diluted with EtOAc, washed with aq., NaHCO3 and water, dried over Na2SO4 and evaporated to dryness in vacuo. After the work-up the residue was purified by automated flash liquid chromatography (Horizon™-Biotage) eluting with PE-EtOAc 8:2. affording the title product (32 mg, 10%).

Workup

  1. customInto a flamed flask flushed with nitrogen
  2. temperatureThe reaction mixture was then cooled to r.t.
  3. washwashed with aq., NaHCO3 and water
  4. dry with materialdried over Na2SO4
  5. customevaporated to dryness in vacuo
  6. customAfter the work-up the residue was purified by automated flash liquid chromatography (Horizon™-Biotage)
  7. washeluting with PE-EtOAc 8:2

Sources & evidence

ORD record
ord-9487ee5ee34645b489a8be11a9b2cc21
Source dataset
uspto-grants-2013_08
Patent number
US08518916B2

Reaction notes

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