Triethylamine → HCID 68542015, compound

HRID 1446680Notes

Reaction equation

HRID 1446680 reaction equation
I[C:2]1[CH:7]=[CH:6][N:5]2[CH:8]=[CH:9][N:10]=[C:4]2[CH:3]=1.[C:11]([Si:13]([CH:20]([CH3:22])[CH3:21])([CH:17]([CH3:19])[CH3:18])[CH:14]([CH3:16])[CH3:15])#[CH:12].C(N(CC)CC)C>O1CCOCC1.[Cu]I.Cl[Pd]Cl>[CH:17]([Si:13]([C:11]#[C:12][C:2]1[CH:7]=[CH:6][N:5]2[CH:8]=[CH:9][N:10]=[C:4]2[CH:3]=1)([CH:14]([CH3:16])[CH3:15])[CH:20]([CH3:21])[CH3:22])([CH3:19])[CH3:18]

Participants

7

Reactant 3

HCID 8471TriethylamineHCID 2734682(Triisopropylsilyl)acetyleneHCID 532499347-Iodoimidazo[1,2-a]pyridine

Product 1

HCID 68542015HCID 68542015, compound

Reagents, catalysts & solvents 3

HCID 24290Palladium ChlorideCatalystHCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
85 °C

Procedure

Combine 7-iodo-imidazo[1,2-a]pyridine (2.64 g, 10.82 mmol), ethynyl-triisopropyl-silane (3.61 mL, 16.23 mmol), copper (I) iodide (0.103 g, 0.541 mmol) and triethylamine (7.54 mL, 54.09 mmol) in 1,4-dioxane (50 mL). Bubble nitrogen through the mixture for five minutes. Add [1,1′-Bis(diphenyl-phosphino)ferrocene] dichloropalladium(II) (0.442 g, 0.541 mmol, 1:1 complex with dichloromethane). Attach a reflux condenser, and heat the mixture to 85° C., stir overnight (15 hours), and cool to room temperature. Filter the mixture through Celite® 521. Concentrate the solution in vacuo to a dark brown oil and use as is. MS(ES), m/z 299 (M+1).

Workup

  1. temperaturecool to room temperature
  2. filtrationFilter the mixture through Celite® 521
  3. concentrationConcentrate the solution in vacuo to a dark brown oil and use

Sources & evidence

ORD record
ord-aafb5c89a76a4ec78005722e7cead945
Source dataset
uspto-grants-2010_02
Patent number
US07666879B2

Reaction notes

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