Trimethylsilylacetylene → 6-[(trimethylsilyl)ethynyl]-1-benzoyl-1H-pyrrolo[2,3-b]pyridine

HRID 1749818Notes

Reaction equation

HRID 1749818 reaction equation
[C:1]([N:9]1[C:13]2=[N:14][C:15](Br)=[CH:16][CH:17]=[C:12]2[CH:11]=[CH:10]1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:19][Si:20]([C:23]#[CH:24])([CH3:22])[CH3:21]>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>[CH3:19][Si:20]([C:23]#[C:24][C:15]1[N:14]=[C:13]2[N:9]([C:1](=[O:8])[C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)[CH:10]=[CH:11][C:12]2=[CH:17][CH:16]=1)([CH3:22])[CH3:21]

Participants

6

Reactant 2

HCID 66111TrimethylsilylacetyleneHCID 150138931-Benzoyl-6-bromo-7-azaindole

Product 1

HCID 156866596-[(trimethylsilyl)ethynyl]-1-benzoyl-1H-pyrrolo[2,3-b]pyridineYield 14.1%

Reagents, catalysts & solvents 3

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

Procedure

The synthesis was performed with reference to the known literature (Bulletin of the Chemical Society of Japan, Vol. 65, p. 2992, 1992). A solution of 1-benzoyl-6-bromo-1H-pyrrolo[2,3-b]pyridine (0.30 g, 1.0 mmol) in triethylamine (25 mL) was added with dichlorobis(triphenylphosphine)palladium(II) (0.036 g, 0.050 mmol), and copper(I) iodide (0.016 g, 0.085 mmol) under an argon atmosphere. Then, the mixture was slowly added with trimethylsilylacetylene (0.20 g, 2.0 mmol), and then the mixture was stirred at room temperature for 24 hours. Triethylamine 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 subjected to silica gel column chromatography (eluted with hexane/ethyl acetate (100:0→90:10)) to obtain 6-[(trimethylsilyl)ethynyl]-1-benzoyl-1H-pyrrolo[2,3-b]pyridine (0.045 g, 14%).

Workup

  1. customTriethylamine 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 subjected to silica gel column chromatography (eluted with hexane/ethyl acetate (100:0→90:10))

Sources & evidence

ORD record
ord-7ccadb1b360e46199b8c46c55c6506c3
Source dataset
uspto-grants-2015_10
Patent number
US09156827B2

Reaction notes

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