Sodium Hydroxide → 6-ethynyl-1H-pyrrolo[2,3-b]pyridine

HRID 1749819Notes

Reaction equation

HRID 1749819 reaction equation
C[Si]([C:5]#[C:6][C:7]1[N:12]=[C:11]2[N:13](C(=O)C3C=CC=CC=3)[CH:14]=[CH:15][C:10]2=[CH:9][CH:8]=1)(C)C.[OH-].[Na+]>CO>[C:6]([C:7]1[N:12]=[C:11]2[NH:13][CH:14]=[CH:15][C:10]2=[CH:9][CH:8]=1)#[CH:5]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 156866596-[(trimethylsilyl)ethynyl]-1-benzoyl-1H-pyrrolo[2,3-b]pyridine

Product 1

HCID 101032716-ethynyl-1H-pyrrolo[2,3-b]pyridineYield 93.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The synthesis was performed with reference to the known literature (Bulletin of Chemical Society of Japan, Vol. 65, p. 2992, 1992). A solution of 6-[(trimethylsilyl)ethynyl]-1-benzoyl-1H-pyrrolo[2,3-b]pyridine (0.039 g, 0.12 mmol) in methanol (2.0 mL) was added with 5 N aqueous sodium hydroxide (1.0 mL), and the mixture was stirred at room temperature for 24 hours. The solvent was evaporated under reduced pressure, the residue was dissolved in ethyl acetate, and then the organic layer was washed successively with water and saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, and the residue was washed with a mixed solvent of hexane and ethyl acetate to obtain 6-ethynyl-1H-pyrrolo[2,3-b]pyridine (0.016 g, 90%).

Workup

  1. customThe solvent was evaporated under reduced pressure
  2. dissolutionthe residue was dissolved in ethyl acetate
  3. washthe organic layer was washed successively with water and saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customThe solvent was evaporated under reduced pressure
  6. washthe residue was washed with a mixed solvent of hexane and ethyl acetate

Sources & evidence

ORD record
ord-aa3ec2b423d1467d97b2ca0bb37891d5
Source dataset
uspto-grants-2015_10
Patent number
US09156827B2

Reaction notes

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