Sulfuric Acid → ethyl 4-chloro-1H-pyrrolo[3,2-c]pyridine-7-carboxylate

HRID 733737

Reaction equation

HRID 733737 reaction equation
[Cl:1][C:2]1[C:7]2[CH:8]=[CH:9][N:10](CC3C=CC(OC)=CC=3)[C:6]=2[C:5]([C:20]([O:22][CH2:23][CH3:24])=[O:21])=[CH:4][N:3]=1.S(=O)(=O)(O)O.C(=O)(O)[O-].[Na+]>C(O)(C(F)(F)F)=O.C1(OC)C=CC=CC=1>[Cl:1][C:2]1[C:7]2[CH:8]=[CH:9][NH:10][C:6]=2[C:5]([C:20]([O:22][CH2:23][CH3:24])=[O:21])=[CH:4][N:3]=1

Participants

6

Reactant 3

HCID 1118Sulfuric AcidHCID 516892Sodium BicarbonateHCID 57840887Ethyl 4-chloro-1-{[4-(methyloxy)phenyl]methyl}-1H-pyrrolo[3,2-c]pyridine-7-carboxylate

Product 1

HCID 57840913ethyl 4-chloro-1H-pyrrolo[3,2-c]pyridine-7-carboxylateYield 37.6%

Reagents, catalysts & solvents 2

HCID 6422Trifluoroacetic acidSolventHCID 7519AnisoleSolvent

Procedure

A solution of ethyl 4-chloro-1-{[4-(methyloxy)phenyl]methyl}-1H-pyrrolo[3,2-c]pyridine-7-carboxylate (2.00 g) in TFA (30 ml), anisole (1.84 ml), and sulphuric acid (15 ml) was stirred at room temperature for 30 minutes. The solution was added to an aqueous saturated sodium bicarbonate solution at 0° C. and extracted with ethyl acetate. The aqueous layer was separated and extracted three times with ethyl acetate. The combined organic layers were washed with brine, dried (MgSO4), filtered and evaporated to afford the title compound as a brown solid (0.49 g).

Workup

  1. extractionextracted with ethyl acetate
  2. customThe aqueous layer was separated
  3. extractionextracted three times with ethyl acetate
  4. washThe combined organic layers were washed with brine
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. customevaporated

Sources & evidence

ORD record
ord-7a8e7dc281884b689847404ccfcb578d
Source dataset
uspto-grants-2009_09
Patent number
US07589206B2

Linked notes

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