Potassium Carbonate → 5-ethynyl-1H-pyrrolo[2,3-b]pyridine

HRID 217595Notes

Reaction equation

HRID 217595 reaction equation
C[Si]([C:5]#[C:6][C:7]1[CH:8]=[C:9]2[CH:15]=[CH:14][NH:13][C:10]2=[N:11][CH:12]=1)(C)C.C(=O)([O-])[O-].[K+].[K+]>CO>[C:6]([C:7]1[CH:8]=[C:9]2[CH:15]=[CH:14][NH:13][C:10]2=[N:11][CH:12]=1)#[CH:5]

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 595696175-((Trimethylsilyl)ethynyl)-1H-pyrrolo[2,3-b]pyridine

Product 1

HCID 552879815-ethynyl-1H-pyrrolo[2,3-b]pyridineYield 99.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

5-Trimethylsilanylethynyl-1H-pyrrolo[2,3-b]pyridine (26, 0.235 g, 1.10 mmol) was dissolved in 16 mL of methanol, and potassium carbonate (0.0152 g, 0.110 mmol) was added. The reaction was stirred for 2 hours at room temperature, then concentrated under vacuum, and the residue was dissolve in dichloromethane, 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 hexane. The appropriate fractions were combined and the solvents removed under vacuum to provide the desired compound as a solid (27, 0.155 g). MS (ESI) [M+H+]+=143.3.

Workup

  1. concentrationconcentrated under vacuum
  2. dissolutionthe residue was dissolve in dichloromethane
  3. dry with materialdried over sodium sulfate
  4. filtrationSolids were filtered out
  5. concentrationthe filtrate was concentrated under vacuum
  6. customThe crude material was purified by silica gel flash chromatography
  7. washeluting with ethyl acetate and hexane
  8. customthe solvents removed under vacuum

Sources & evidence

ORD record
ord-d7022b4bcb714bbd81649239494e5896
Source dataset
uspto-grants-2012_06
Patent number
US08198273B2

Reaction notes

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