Triethylamine → HCID 19002927, compound

HRID 2259505Notes

Reaction equation

HRID 2259505 reaction equation
I[C:2]1[C:7]([OH:8])=[CH:6][CH:5]=[C:4](C)[N:3]=1.[CH3:10][Si:11]([C:14]#[CH:15])([CH3:13])[CH3:12].[CH3:16]CN(CC)CC>CCOCC.[Cu]I.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.Cl[Pd]Cl>[CH3:10][Si:11]([CH3:13])([CH3:12])[C:14]1[O:8][C:7]2[C:2](=[N:3][CH:4]=[C:5]([CH3:16])[CH:6]=2)[CH:15]=1

Participants

7

Reactant 3

HCID 8471TriethylamineHCID 66111TrimethylsilylacetyleneHCID 899572-Iodo-6-methylpyridin-3-ol

Product 1

HCID 19002927HCID 19002927, compoundYield 86%

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 6102075Dichlorobis(triphenylphosphine)palladiumCatalystHCID 3283Diethyl EtherSolvent

Procedure

A mixture of 2-iodo-6-methylpyridine-3-ol (20 g, 85 mmol), CuI (2.1 g, 11 mmol), trimethylsilyl acetylene (23.4 g, 238 mmol), and bis(triphenylphosphine)palladium(II)chloride (5.37 g, 7.65 mmol) in Et3N (380 mL) was heated to reflux for 20 hr. The mixture was cooled and diluted with ether and filtered through celite. The filtrate was concentrated in vacuo and the residue was chromatographed on silica gel (eluted with 10% EtOAc in hexane) to give 15 g (86%) of the title compound.

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 20 hr
  3. temperatureThe mixture was cooled
  4. filtrationfiltered through celite
  5. concentrationThe filtrate was concentrated in vacuo
  6. customthe residue was chromatographed on silica gel (eluted with 10% EtOAc in hexane)

Sources & evidence

ORD record
ord-6dd2fa9b14b54459adc2f47cf1fb15b5
Source dataset
uspto-grants-1995_12
Patent number
US05472964

Reaction notes

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