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Trimethylsilylacetylene → 3-Bromo-5-((trimethylsilyl)ethynyl)pyridine

HRID 606803
Notes
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Reaction equation

HRID 606803 reaction equation
[CH3:1][Si:2]([C:5]#[CH:6])([CH3:4])[CH3:3].[Br:7][C:8]1[CH:9]=[N:10][CH:11]=[C:12](I)[CH:13]=1>C(N(CC)CC)C.C(#N)C.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>[Br:7][C:8]1[CH:9]=[N:10][CH:11]=[C:12]([C:6]#[C:5][Si:2]([CH3:4])([CH3:3])[CH3:1])[CH:13]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 2

HCID 66111TrimethylsilylacetyleneHCID 8204093-Bromo-5-iodopyridine

Product 1

HCID 665244243-Bromo-5-((trimethylsilyl)ethynyl)pyridineYield 99%

Reagents, catalysts & solvents 3

HCID 178418476HCID 178418476, compoundCatalystHCID 6342AcetonitrileSolvent
HCID 8471
Triethylamine
Solvent

Procedure

Add trimethylsilylacetylene (54.6 mL, 389.4 mmol) to a stirred mixture of 3-bromo-5-iodopyridine (100 g, 354 mmol) in triethylamine (800 mL) and acetonitrile (800 mL). Purge the system with nitrogen and add bis(triphenylphosphine)palladium(II) dichloride (3.54 mmol, 2.48 g) and stir for 16 h. Concentrate and suspend the residue in 1800 mL of hexanes. Stir for 2 h, filter and concentrate to give the title compound as a brown solid (92g, 99%).

Workup

  1. customPurge the system with nitrogen
  2. concentrationConcentrate
  3. stirringStir for 2 h
  4. filtrationfilter
  5. concentrationconcentrate

Sources & evidence

ORD record
ord-96c71ebfff6c4ee8bb6a5aa2960c2ba3
Source dataset
uspto-grants-2011_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07915424B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes