5-Nitro-3-trimethylsilanylethynyl-pyridin-2-ylamine → 5-Nitro-7-azaindole

HRID 1515846Notes

Reaction equation

HRID 1515846 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([C:11]#[C:12][Si](C)(C)C)[C:7]([NH2:10])=[N:8][CH:9]=1)([O-:3])=[O:2]>CN(C)C(=O)C.[Cu]I>[N+:1]([C:4]1[CH:5]=[C:6]2[CH:11]=[CH:12][NH:10][C:7]2=[N:8][CH:9]=1)([O-:3])=[O:2]

Participants

4

Reactant 1

HCID 115287895-Nitro-3-trimethylsilanylethynyl-pyridin-2-ylamine

Product 1

HCID 115211405-Nitro-7-azaindoleYield 83%

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 31374DimethylacetamideSolvent

Procedure

5-Nitro-3-trimethylsilanylethynyl-pyridin-2-ylamine (0.7 g, 2.98 mmol) and copper(I) iodide (114 mg, 0.60 mmol) were dissolved in N,N-dimethylacetamide (14 mL). The mixture was irradiated in a microwave reactor at 190° C. for 30 min. The mixture was evaporated to remove N,N-dimethylacetamide in vacuo. The residue was dissolved in hot tetrahydrofuran (50° C., 250 mL) and filtered through a short pad of silica gel (from QingDao, 200-300 mesh). The filtrate was concentrated to afford 5-nitro-1H-pyrrolo[2,3-b]pyridine (0.4 g, 83%) as a yellow solid: LC/MS m/e calcd for C7H5N3O2 [M+H]+ 164.14, observed 164.0.

Workup

  1. customThe mixture was irradiated in a microwave reactor at 190° C. for 30 min
  2. customThe mixture was evaporated
  3. customto remove N,N-dimethylacetamide in vacuo
  4. dissolutionThe residue was dissolved in hot tetrahydrofuran (50° C., 250 mL)
  5. filtrationfiltered through a short pad of silica gel (from QingDao, 200-300 mesh)
  6. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-480b05c767f5451eb51629b3358264c1
Source dataset
uspto-grants-2012_07
Patent number
US08222416B2

Reaction notes

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