Triethylamine → 3-Methoxy-5-[(trimethylsilyl)ethynyl]pyridine

HRID 606789Notes

Reaction equation

HRID 606789 reaction equation
[CH3:1][Si:2]([C:5]#[CH:6])([CH3:4])[CH3:3].Br[C:8]1[CH:9]=[N:10][CH:11]=[C:12]([O:14][CH3:15])[CH:13]=1.C(N(CC)CC)C>C(OCC)(=O)C.C1(C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)[Pd][P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.[Cu]I>[CH3:15][O:14][C:12]1[CH:11]=[N:10][CH:9]=[C:8]([C:6]#[C:5][Si:2]([CH3:4])([CH3:3])[CH3:1])[CH:13]=1

Participants

7

Reactant 3

HCID 8471TriethylamineHCID 66111TrimethylsilylacetyleneHCID 8171633-Bromo-5-methoxypyridine

Product 1

HCID 670475633-Methoxy-5-[(trimethylsilyl)ethynyl]pyridine

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178419050HCID 178419050, compoundCatalystHCID 8857Ethyl AcetateSolvent2×

Procedure

Add (trimethylsilyl)acetylene (1.3 mL, 9.45 mmol) and bis(triphenylphosphine)palladium (II) dichloride (0.102 g, 0.15 mmol) to a mixture of 3-bromo-5-methoxypyridine from PREPARATION 9 (1.366 g, 7.26 mmol), copper (I) iodide (0.055 g, 0.29 mmol) and triethylamine (4.1 mL, 29.04 mmol) in ethyl acetate (7.5 mL) in a sealed tube. Stir the resultant reaction mixture at 75° C. for 20 h and cool to room temperature. Dilute the reaction mixture with ethyl acetate and filter through a pad of diatomaceous earth. Wash with ethyl acetate and concentrate the filtrate to give the title compound as a solid which is used without further purification (1.48 g, 100%).

Workup

  1. customreaction mixture at 75° C. for 20 h
  2. filtrationfilter through a pad of diatomaceous earth
  3. washWash with ethyl acetate
  4. concentrationconcentrate the filtrate

Sources & evidence

ORD record
ord-afa1e171168c4bdf838f91f40800a3ce
Source dataset
uspto-grants-2011_03
Patent number
US07915424B2

Reaction notes

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