p-Toluenesulphonyl cyanide → HCID 49758988, compound

HRID 1696203Notes

Reaction equation

HRID 1696203 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]2[N:8]([Si:11]([CH:18]([CH3:20])[CH3:19])([CH:15]([CH3:17])[CH3:16])[CH:12]([CH3:14])[CH3:13])[CH:9]=[CH:10][C:3]=12.C([Li])(CC)C.CC1C=CC(S([C:36]#[N:37])(=O)=O)=CC=1>O1CCCC1.CCCCCC>[Cl:1][C:2]1[C:7]([C:36]#[N:37])=[CH:6][N:5]=[C:4]2[N:8]([Si:11]([CH:15]([CH3:17])[CH3:16])([CH:18]([CH3:20])[CH3:19])[CH:12]([CH3:13])[CH3:14])[CH:9]=[CH:10][C:3]=12

Participants

6

Reactant 3

HCID 87946p-Toluenesulphonyl cyanideHCID 114382724-Chloro-1-(triisopropylsilyl)-1H-pyrrolo[2,3-b]pyridineHCID 178418400CID 53628100

Product 1

HCID 49758988HCID 49758988, compoundYield 33.7%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8058HexaneSolvent

Procedure

To a solution of 4-chloro-1-(triisopropylsilyl)-1H-pyrrolo-[2,3-b]pyridine (1.22 g) in tetrahydrofuran (12.2 mL) was added 0.95M sec-butyl lithium in n-hexane (8.3 mL) dropwise at −78° C. The mixture was stirred at the same temperature for 1 hour. To the solution was added 4-methylbenzenesulfonyl cyanide (1.43 g) and the mixture was stirred at ambient temperature for 2 hours. The reaction mixture was quenched with saturated aqueous ammonium chloride solution and extracted with EtOAc. The extract was washed with water and brine, dried over MgSO4, filtrated and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel with EtOAc and n-hexane to give 4-chloro-1-(triisopropylsilyl)-1H-pyrrolo[2,3-b]pyridine-5-carbonitrile (444 mg) as a white solid.

Workup

  1. stirringthe mixture was stirred at ambient temperature for 2 hours
  2. customThe reaction mixture was quenched with saturated aqueous ammonium chloride solution
  3. extractionextracted with EtOAc
  4. washThe extract was washed with water and brine
  5. dry with materialdried over MgSO4
  6. filtrationfiltrated
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was purified by column chromatography on silica gel with EtOAc and n-hexane

Sources & evidence

ORD record
ord-ed05430eadbe43cdbd676128879c5e33
Source dataset
uspto-grants-2012_04
Patent number
US08163767B2

Reaction notes

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