Carbon Dioxide → 7-chloro-1H-pyrrolo[2,3-c]pyridine-4-carboxylic acid

HRID 733678Notes

Reaction equation

HRID 733678 reaction equation
Br[C:2]1[CH:7]=[N:6][C:5]([Cl:8])=[C:4]2[N:9]([Si](C(C)(C)C)(C)C)[CH:10]=[CH:11][C:3]=12.C([Li])(C)(C)C.[C:24](=[O:26])=[O:25]>O1CCCC1>[Cl:8][C:5]1[C:4]2[NH:9][CH:10]=[CH:11][C:3]=2[C:2]([C:24]([OH:26])=[O:25])=[CH:7][N:6]=1

Participants

5

Reactant 3

HCID 280Carbon DioxideHCID 578410104-Bromo-1-(tert-butyl-dimethyl-silanyl)-7-chloro-1H-pyrrolo[2,3-c]pyridineHCID 178418306HCID 178418306, compound

Product 1

HCID 578408437-chloro-1H-pyrrolo[2,3-c]pyridine-4-carboxylic acid

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

To a solution of 4-bromo-1-(tert-butyl-dimethyl-silanyl)-7-chloro-1H-pyrrolo[2,3-c]pyridine (500 mg) in dry tetrahydrofuran (25 ml) at −78° C. under an atmosphere of nitrogen was added tert-butyllithium (1.7M in pentane, 1.88 ml). After addition, the reaction mixture was stirred for 15 minutes at −78° C. then poured onto crushed pellets of carbon dioxide. The mixture was allowed to warm to room temperature and then evaporated. The residue was dissolved in water and the aqueous washed twice with diethyl ether. The aqueous was then acidified with 2M hydrochloric acid and extracted twice with ethyl acetate. The organic layer was dried (MgSO4) and evaporated to give the title compound as a yellow solid (120 mg).

Workup

  1. additionAfter addition
  2. additionthen poured
  3. temperatureto warm to room temperature
  4. customevaporated
  5. dissolutionThe residue was dissolved in water
  6. washthe aqueous washed twice with diethyl ether
  7. extractionextracted twice with ethyl acetate
  8. dry with materialThe organic layer was dried (MgSO4)
  9. customevaporated

Sources & evidence

ORD record
ord-12470fe571574d89a2249cd435bc27bb
Source dataset
uspto-grants-2009_09
Patent number
US07589206B2

Reaction notes

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