Water → 2-bromo-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[2,3-b]pyrazine-7-carbaldehyde

HRID 716051Notes

Reaction equation

HRID 716051 reaction equation
[Br:1][C:2]1[N:3]=[C:4]2[C:10]([CH:11]=[O:12])=[CH:9][NH:8][C:5]2=[N:6][CH:7]=1.[H-].[Na+].[CH3:15][Si:16]([CH2:19][CH2:20][O:21][CH2:22]Cl)([CH3:18])[CH3:17].O>CN(C=O)C>[Br:1][C:2]1[N:3]=[C:4]2[C:10]([CH:11]=[O:12])=[CH:9][N:8]([CH2:22][O:21][CH2:20][CH2:19][Si:16]([CH3:18])([CH3:17])[CH3:15])[C:5]2=[N:6][CH:7]=1

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 27242712-Chloromethyl 2-(trimethylsilyl)ethyl etherHCID 575165872-Bromo-5H-pyrrolo[2,3-b]pyrazine-7-carbaldehyde

Product 1

HCID 578296122-bromo-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[2,3-b]pyrazine-7-carbaldehydeYield 21.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a 10 ml round bottom flask, 2-bromo-5H-pyrrolo[2,3-b]pyrazine-7-carbaldehyde (0.450 g, 0.00199 mol) and NaH (0.143 g, 0.00597 mol) were taken in DMF (5 ml) and stirred in cooling for 15 min. SEM-Cl (0.497 g, 0.00298 mol) was added dropwise and stirred at room temperature for 2 hr. After completion of the reaction, the reaction mixture was poured in to water and extracted with ethyl acetate. The combined organics were washed with brine solution. The organic layer was separated and dried over sodium sulphate, concentrated to give the crude product which was purified using column purification by eluting the compound with 10% ethyl acetate in hexanes to yield 150 mg of 2-bromo-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[2,3-b]pyrazine-7-carbaldehyde.

Workup

  1. temperaturein cooling for 15 min
  2. stirringstirred at room temperature for 2 hr
  3. customAfter completion of the reaction
  4. extractionextracted with ethyl acetate
  5. washThe combined organics were washed with brine solution
  6. customThe organic layer was separated
  7. dry with materialdried over sodium sulphate
  8. concentrationconcentrated
  9. customto give the crude product which
  10. customwas purified
  11. customcolumn purification
  12. washby eluting the compound with 10% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-cf2ae23aab574fd797f283de69195ccf
Source dataset
uspto-grants-2015_11
Patent number
US09187487B2

Reaction notes

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