Triethylamine → 5-Bromo-2-[2-(trimethylsilyl)ethynyl]pyridine

HRID 735056Notes

Reaction equation

HRID 735056 reaction equation
C(N(CC)CC)C.Br[C:9]1[CH:14]=[CH:13][C:12]([Br:15])=[CH:11][N:10]=1.[CH3:16][Si:17]([C:20]#[CH:21])([CH3:19])[CH3:18]>C1COCC1.[Cu]I>[Br:15][C:12]1[CH:13]=[CH:14][C:9]([C:21]#[C:20][Si:17]([CH3:19])([CH3:18])[CH3:16])=[N:10][CH:11]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 66111TrimethylsilylacetyleneHCID 693532,5-Dibromopyridine

Product 1

HCID 109995845-Bromo-2-[2-(trimethylsilyl)ethynyl]pyridine

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
20 °C

Procedure

1.15 g (1.63 mmol) of tetrakistriphenylphosphine palladium, 0.311 g (1.63 mmol) of copper (1) iodide, and 50 mL of triethylamine are added to a solution of 20 g (81.89 mmol) of 2,5-dibromopyridine in 250 mL of absolute THF under an argon atmosphere. At 17° C., a solution of 13 mL (90.14 mmol) of trimethylsilylacetylene in 20 mL of THF is immediately added dropwise to this reaction mixture. After ten minutes, the cooling is removed. After 20 minutes, the temperature is 30° C. The mixture is then cooled to 20° C. and briefly stirred. The reaction mixture is evaporated down, the residue is taken up in ethyl acetate and extracted twice with sodium hydrogen carbonate solution. The combined organic phases are dried over magnesium sulfate. The purification is carried out by column chromatography on silica gel (eluant: petroleum ether). Yield: 20.4 g (98% of theory); C10H12BrNSi (M=254.20); calc.: molecular ion peak (M+H)+: 254/256; found: molecular ion peak (M+H)+: 254/256; Rf value: 0.72 (silica gel, petroleum ether).

Workup

  1. waitAfter ten minutes
  2. customthe cooling is removed
  3. customis 30° C
  4. customThe reaction mixture is evaporated down
  5. extractionextracted twice with sodium hydrogen carbonate solution
  6. dry with materialThe combined organic phases are dried over magnesium sulfate
  7. customThe purification

Sources & evidence

ORD record
ord-2934917fd23b4101b29458970a8c3177
Source dataset
uspto-grants-2009_09
Patent number
US07592373B2

Reaction notes

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