2,3-Dichloro-5,6-dicyano-1,4-benzoquinone → 1-(tert-butyl-dimethyl-silanyl)-5-ethylsulfanyl-1H-pyrrolo[2,3-b]pyridine

HRID 1515900Notes

Reaction equation

HRID 1515900 reaction equation
[C:1]([Si:5]([CH3:19])([CH3:18])[N:6]1[C:10]2=[N:11][CH:12]=[C:13]([S:15][CH2:16][CH3:17])[CH:14]=[C:9]2[CH2:8][CH2:7]1)([CH3:4])([CH3:3])[CH3:2].ClC1C(=O)C(C#N)=C(C#N)C(=O)C=1Cl>ClCCl>[C:1]([Si:5]([CH3:19])([CH3:18])[N:6]1[C:10]2=[N:11][CH:12]=[C:13]([S:15][CH2:16][CH3:17])[CH:14]=[C:9]2[CH:8]=[CH:7]1)([CH3:3])([CH3:4])[CH3:2]

Participants

4

Reactant 2

HCID 67752,3-Dichloro-5,6-dicyano-1,4-benzoquinoneHCID 672289921-(tert-butyl-dimethyl-silanyl)-5-ethylsulfanyl-2,3-dihydro-1H-pyrrolo[2,3-b]pyridine

Product 1

HCID 672294871-(tert-butyl-dimethyl-silanyl)-5-ethylsulfanyl-1H-pyrrolo[2,3-b]pyridineYield 23%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 1-(tert-butyl-dimethyl-silanyl)-5-ethylsulfanyl-2,3-dihydro-1H-pyrrolo[2,3-b]pyridine (2.2 g, 7.6 mmol) in dichloromethane (50 mL) was added 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (2.07 g, 9.1 mmol) at room temperature. After stirring for 12 h at room temperature, the mixture was concentrated. The residue. was purified by flash column chromatography (Qingdao silica gel, 300 mesh, 11% dichloromethane/hexanes) to afford 1-(tert-butyl-dimethyl-silanyl)-5-ethylsulfanyl-1H-pyrrolo[2,3-b]pyridine (0.5 g, 23%) as a yellow oil: LC/MS m/e calcd for C15H24N2SSi [M+H]+ 292.52.

Workup

  1. concentrationthe mixture was concentrated
  2. customwas purified by flash column chromatography (Qingdao silica gel, 300 mesh, 11% dichloromethane/hexanes)

Sources & evidence

ORD record
ord-408f593a7cd94d8991711fe89c94c685
Source dataset
uspto-grants-2012_07
Patent number
US08222416B2

Reaction notes

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