Triethylsilane → Methyl 2-(1H-pyrrolo[2,3-b]pyridin-3-yl)acetate

HRID 1036627Notes

Reaction equation

HRID 1036627 reaction equation
C([SiH](CC)CC)C.O=[C:9]([C:14]1[C:22]2[C:17](=[N:18][CH:19]=[CH:20][CH:21]=2)[NH:16][CH:15]=1)[C:10]([O:12][CH3:13])=[O:11]>C(O)(C(F)(F)F)=O>[NH:16]1[C:17]2=[N:18][CH:19]=[CH:20][CH:21]=[C:22]2[C:14]([CH2:9][C:10]([O:12][CH3:13])=[O:11])=[CH:15]1

Participants

4

Reactant 2

HCID 12052TriethylsilaneHCID 6028556Methyl 7-azaindole-3-glyoxylate

Product 1

HCID 25067325Methyl 2-(1H-pyrrolo[2,3-b]pyridin-3-yl)acetateYield 75.2%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

To a mixture of triethylsilane (9.95 g, 85.78 mmol) in TFA (25 mL) was added portionwise methyl oxo(1H-pyrrolo[2,3-b]pyridin-3-yl)acetate (5.0 g, 24.48 mmol). After a period of 18 h at 50° C., the solvent was evaporated and saturated NaHCO3 was added followed by DCM. The organic phase was separated, dried over magnesium sulfate, filtered and evaporated under reduced pressure. The residue was purified by combiflash with 10% ethyl acetate in hexane to 100% ethyl acetate to provide 3.5 g of the title compound.

Workup

  1. customthe solvent was evaporated
  2. additionsaturated NaHCO3 was added
  3. customThe organic phase was separated
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. customevaporated under reduced pressure
  7. customThe residue was purified by combiflash with 10% ethyl acetate in hexane to 100% ethyl acetate

Sources & evidence

ORD record
ord-47bde9a8ad6748d9986c78ccbceaf641
Source dataset
uspto-grants-2013_10
Patent number
US08546422B2

Reaction notes

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