Triisopropylsilyl chloride → HCID 57830996, compound

HRID 1642070Notes

Reaction equation

HRID 1642070 reaction equation
[Cl:1][C:2]1[N:3]=[C:4]2[C:10]([I:11])=[CH:9][NH:8][C:5]2=[N:6][CH:7]=1.[CH:12]([Si:15](Cl)([CH:19]([CH3:21])[CH3:20])[CH:16]([CH3:18])[CH3:17])([CH3:14])[CH3:13]>O1CCCC1.C(OCC)(=O)C>[Cl:1][C:2]1[N:3]=[C:4]2[C:10]([I:11])=[CH:9][N:8]([Si:15]([CH:19]([CH3:21])[CH3:20])([CH:16]([CH3:18])[CH3:17])[CH:12]([CH3:14])[CH3:13])[C:5]2=[N:6][CH:7]=1

Participants

5

Reactant 2

HCID 139400Triisopropylsilyl chlorideHCID 536276902-Chloro-7-iodo-5H-pyrrolo[2,3-b]pyrazine

Product 1

HCID 57830996HCID 57830996, compoundYield 95%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

A solution of the 2-Chloro-7-iodo-5H-pyrrolo[2,3-b]pyrazine from the previous step in 30 mL of tetrahydrofuran stirring at 0° C. under argon atmosphere was treated with lithium hexamethyldisilylazide (6 mL, 1 M in hexanes, 6 mmol), followed by triisopropylsilyl chloride (1.1 mL, 5.2 mmol). After 30 m at 0° C., the solution was warmed to ambient temperature and diluted with 20% ethyl acetate in hexanes, then washed twice with water and once with brine. After drying the organic layer over magnesium sulfate, filtration was followed by solvent removal and flash chromatography of the resultant residue using 2.5% ethyl acetate in hexanes, to furnish 2-Chloro-7-iodo-5-triisopropylsilanyl-5H-pyrrolo[2,3-b]pyrazine (1.68 g, 95% over two steps).

Workup

  1. washwashed twice with water and once with brine
  2. customAfter drying the organic layer
  3. filtrationover magnesium sulfate, filtration
  4. customwas followed by solvent removal and flash chromatography of the resultant residue

Sources & evidence

ORD record
ord-4bb39287e5954cb5ba01a03605858fe1
Source dataset
uspto-grants-2012_02
Patent number
US08119636B2

Reaction notes

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