Triethylamine → 5-((Trimethylsilyl)ethynyl)-1H-pyrrolo[2,3-b]pyridine

HRID 217594Notes

Reaction equation

HRID 217594 reaction equation
I[C:2]1[CH:3]=[C:4]2[CH:10]=[CH:9][NH:8][C:5]2=[N:6][CH:7]=1.[CH3:11][Si:12]([C:15]#[CH:16])([CH3:14])[CH3:13].C(N(CC)CC)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.[Cu]I>[CH3:11][Si:12]([C:15]#[C:16][C:2]1[CH:3]=[C:4]2[CH:10]=[CH:9][NH:8][C:5]2=[N:6][CH:7]=1)([CH3:14])[CH3:13]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 66111TrimethylsilylacetyleneHCID 242292145-Iodo-1H-pyrrolo[2,3-b]pyridine

Product 1

HCID 595696175-((Trimethylsilyl)ethynyl)-1H-pyrrolo[2,3-b]pyridineYield 90.6%

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418476HCID 178418476, compoundCatalyst

Conditions

Temperature
60 °C

Procedure

5-Iodo-1H-pyrrolo[2,3-b]pyridine (24, 0.303 g, 1.22 mmol), (trimethylsilyl)acetylene (25, 0.210 mL, 1.46 mmol), bis(triphenylphosphine)palladium(II) chloride (0.039 g, 0.055 mmol), and copper(I) iodide (0.0019 g, 0.010 mmol) were dissolved in triethylamine (19 mL, 0.14 mol) under an atmosphere of nitrogen. The resulting mixture was heated to 60° C. and stirred under an atmosphere of nitrogen for 16 hours. The triethylamine was removed under vacuum, 30 mL of water was added to the residue, and it was extracted with 2×20 mL with ether. The combined organic layers were washed with brine and dried over sodium sulfate. Solids were filtered out and the filtrate was concentrated under vacuum. The crude material was purified by silica gel flash chromatography, eluting with ethyl acetate and dichloromethane. The appropriate fractions were combined and the solvents removed under vacuum to provide the desired compound as a solid (26, 0.237 g). MS (ESI) [M+H+]+=215.3.

Workup

  1. customThe triethylamine was removed under vacuum, 30 mL of water
  2. additionwas added to the residue, and it
  3. extractionwas extracted with 2×20 mL with ether
  4. washThe combined organic layers were washed with brine
  5. dry with materialdried over sodium sulfate
  6. filtrationSolids were filtered out
  7. concentrationthe filtrate was concentrated under vacuum
  8. customThe crude material was purified by silica gel flash chromatography
  9. washeluting with ethyl acetate and dichloromethane
  10. customthe solvents removed under vacuum

Sources & evidence

ORD record
ord-0bb2d059b56c4deb859c06bff6b845fa
Source dataset
uspto-grants-2012_06
Patent number
US08198273B2

Reaction notes

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