Trimethylsilylacetylene → 6-((Trimethylsilyl)ethynyl)isoquinoline

HRID 598839Notes

Reaction equation

HRID 598839 reaction equation
Br[C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]=[N:7][CH:6]=[CH:5]2.[C:12]([Si:14]([CH3:17])([CH3:16])[CH3:15])#[CH:13]>CCN(CC)CC.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.[Cu]I>[CH3:15][Si:14]([CH3:17])([CH3:16])[C:12]#[C:13][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]=[N:7][CH:6]=[CH:5]2

Participants

6

Reactant 2

HCID 66111TrimethylsilylacetyleneHCID 3136816-Bromoisoquinoline

Product 1

HCID 579505646-((Trimethylsilyl)ethynyl)isoquinolineYield 101.7%

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418476HCID 178418476, compoundCatalystHCID 8471TriethylamineSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of 6-bromoisoquinoline (2.0 g, 9.6 mmol) (commercially available from Gateway Chemical Technology, Inc.) in 45 mL of Et3N was added PdCl2(PPh3)2 (0.34 g, 0.48 mmol) and copper(I) iodide (0.27 g, 1.4 mmol). The mixture was degassed by bubbling nitrogen through the mixture for 1 minute. Ethynyltrimethylsilane (2.7 mL, 19 mmol) was added. The mixture was heated to 50° C. After 1 hour, the solvent was removed by rotary evaporation and the residue was purified by flash chromatography on silica gel (5% to 30% EtOAc/hexanes), affording 6-(2-(trimethylsilyl)ethynyl)isoquinoline (2.2 g, 100% yield).

Workup

  1. customThe mixture was degassed
  2. customby bubbling nitrogen through the mixture for 1 minute
  3. customthe solvent was removed by rotary evaporation
  4. customthe residue was purified by flash chromatography on silica gel (5% to 30% EtOAc/hexanes)

Sources & evidence

ORD record
ord-6cc7540067a14f68abf611ed448f0765
Source dataset
uspto-grants-2011_03
Patent number
US07897619B2

Reaction notes

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