Triethylamine → 5-Ethoxycarbonyl-2-trimethylsilylethynylpyridine

HRID 1838348

Reaction equation

HRID 1838348 reaction equation
[CH2:1]([O:3][C:4](=[O:12])[C:5]1[CH:10]=[CH:9][C:8](Cl)=[N:7][CH:6]=1)[CH3:2].[CH3:13][Si:14]([C:17]#[CH:18])([CH3:16])[CH3:15].C(N(CC)CC)C.C(=O)([O-])O.[Na+]>CN(C)C=O>[CH2:1]([O:3][C:4]([C:5]1[CH:10]=[CH:9][C:8]([C:18]#[C:17][Si:14]([CH3:16])([CH3:15])[CH3:13])=[N:7][CH:6]=1)=[O:12])[CH3:2]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 66111TrimethylsilylacetyleneHCID 516892Sodium BicarbonateHCID 2799611Ethyl 6-chloronicotinate

Product 1

HCID 225043975-Ethoxycarbonyl-2-trimethylsilylethynylpyridineYield 93%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of 6-chloronicotinic acid ethyl ester (1.92 g) in N,N-dimethylformamide (1 ml), trimethylsilylacetylene (2.0 g), bistriphenylphosphine palladium dichloride (210 mg), cuprous iodide (60 mg) and triethylamine (1.2 g) were added successively and the mixture was stirred in a sealed tube at 100° C. for 2 hours. After cooling, the reaction solution was poured into a saturated aqueous sodium hydrogencabonate solution, extracted with ethyl acetate, dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure. The resulting residue was separated using silica gel column chromatography (hexane:ethyl acetate=10:1) to obtain 2.38 g of the desired product as a brown oil.

Workup

  1. temperatureAfter cooling
  2. extractionextracted with ethyl acetate
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe resulting residue was separated

Sources & evidence

ORD record
ord-e69a9670664c44de86b0d37c655679a2
Source dataset
uspto-grants-2004_01
Patent number
US06673797B1

Linked notes

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