Triethylamine → HCID 19002927, compound

HRID 1492410Notes

Reaction equation

HRID 1492410 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 flitrate 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. 1H NMR (CD3COCD3) δ 0.40 (9H, s), 2.54 (3H, s), 7.12 (1H, d, J=8 Hz), 7.14 (1H, s), 7.75 (1H, d, J=8 Hz).

Workup

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

Sources & evidence

ORD record
ord-e6aa420505a04c74ac6c0c1acd4a72ac
Source dataset
uspto-grants-1994_12
Patent number
US05374635

Reaction notes

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