Triethylamine → HCID 67486279, compound

HRID 1523573Notes

Reaction equation

HRID 1523573 reaction equation
[C:1]([O:4][C:5]1[C:6](Br)=[N:7][CH:8]=[CH:9][CH:10]=1)(=[O:3])[CH3:2].C(N(CC)CC)C.[C:19]([Si:21]([CH3:24])([CH3:23])[CH3:22])#[CH:20]>C1COCC1.[Cu]I.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[C:1]([O:4][C:5]1[C:6]([C:20]#[C:19][Si:21]([CH3:24])([CH3:23])[CH3:22])=[N:7][CH:8]=[CH:9][CH:10]=1)(=[O:3])[CH3:2]

Participants

7

Reactant 3

HCID 8471TriethylamineHCID 66111TrimethylsilylacetyleneHCID 154718962-Bromopyridin-3-yl acetate

Product 1

HCID 67486279HCID 67486279, compoundYield 89.1%

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418476HCID 178418476, compoundCatalystHCID 8028TetrahydrofuranSolvent

Procedure

2-Bromopyridin-3-yl acetate (10 g, 46 mmol) was dissolved in THF (80 mL) and triethylamine (32 ml, 231 mmol), ethynyltrimethylsilane (19.5 ml, 139 mmol), and CuI (0.44 g, 2.3 mmol) were added. The mixture was degassed with argon for 15 minutes, then PdCl2(PPh3)2 (1.6 g, 2.3 mmol) was added and the mixture was stirred under argon at ambient temperature for 18 hours. The reaction was concentrated in vacuo, dissolved in 25% EtOAc in hexanes, filtered and purified over silica gel (25% ethyl acetate/hexanes) to afford 2-((trimethylsilyl)ethynyl)pyridin-3-yl acetate (9.7 g, 41 mmol).

Workup

  1. customThe mixture was degassed with argon for 15 minutes
  2. concentrationThe reaction was concentrated in vacuo
  3. dissolutiondissolved in 25% EtOAc in hexanes
  4. filtrationfiltered
  5. custompurified over silica gel (25% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-7a35a46ea254409494a073b1cc2d1eee
Source dataset
uspto-grants-2015_07
Patent number
US09079890B2

Reaction notes

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