Sodium Carbonate → 1-(tert-Butyl-dimethyl-silanyl)-5-pyridin-3-yl-1H-pyrrolo[2,3-b]pyridine

HRID 1024396Notes

Reaction equation

HRID 1024396 reaction equation
Br[C:2]1[CH:3]=[C:4]2[CH:10]=[CH:9][N:8]([Si:11]([C:14]([CH3:17])([CH3:16])[CH3:15])([CH3:13])[CH3:12])[C:5]2=[N:6][CH:7]=1.C(=O)([O-])[O-].[Na+].[Na+]>COCCOC.C(OCC)(=O)C>[C:14]([Si:11]([CH3:13])([CH3:12])[N:8]1[C:5]2=[N:6][CH:7]=[C:2]([C:4]3[CH:5]=[N:6][CH:7]=[CH:2][CH:3]=3)[CH:3]=[C:4]2[CH:10]=[CH:9]1)([CH3:17])([CH3:16])[CH3:15]

Participants

5

Reactant 2

HCID 10340Sodium CarbonateHCID 497590181H-Pyrrolo[2,3-B]pyridine, 5-bromo-1-[(1,1-dimethylethyl)dimethylsilyl]-

Product 1

HCID 575980361-(tert-Butyl-dimethyl-silanyl)-5-pyridin-3-yl-1H-pyrrolo[2,3-b]pyridineYield 113.4%

Reagents, catalysts & solvents 2

HCID 80711,2-DimethoxyethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 19 (1.77 g, 0.0057 mol), 3-diethylpyridyl borane (1.0 g, 0.0068 mol) in 80 mL of DME, was added PdCl2(Ph3P)2 (320 mg, 0.455 mmol) and aqueous 2M sodium carbonate (8.5 mL, 0.017 mol) under nitrogen. The reaction mixture was refluxed for 3 h. Cooled to rt and diluted with ethyl acetate and washed with brine. The organic layer was dried and concentrated to an oil that was subjected to flash chromatography (30% EtOAc-70% hexanes) to give 1 g (57%) of the desired material 20. 1H NMR CDCl3 8.9 (s, 1H), 8.5 (d, 1H), 8.4 (d, 1H), 8.0 (d, 1H), 7.9 (d, 1H), 7.5 (d, 1H), 7.2 (d, 1H), 6.5 (d, 1H), 0.85 (s, 9H), 0.55 (s, 6H).

Workup

  1. temperatureThe reaction mixture was refluxed for 3 h
  2. washwashed with brine
  3. customThe organic layer was dried
  4. concentrationconcentrated to an oil that

Sources & evidence

ORD record
ord-85c5155b5b304a1db43cd9297d3aa45f
Source dataset
uspto-grants-2014_05
Patent number
US08722889B2

Reaction notes

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