Sulfuric Acid → 5-Benzyloxy-1H-pyrrolo[2,3-b]pyridine-2-carboxylic acid methyl ester

HRID 506758Notes

Reaction equation

HRID 506758 reaction equation
C(OC([N:8]1[C:12]2=[N:13][CH:14]=[C:15]([O:17][CH2:18][C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[CH:16]=[C:11]2[CH:10]=[C:9]1[C:25]([OH:27])=[O:26])=O)(C)(C)C.S(=O)(=O)(O)O.[C:33](=O)(O)[O-].[Na+]>CO>[CH3:33][O:27][C:25]([C:9]1[NH:8][C:12]2=[N:13][CH:14]=[C:15]([O:17][CH2:18][C:19]3[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=3)[CH:16]=[C:11]2[CH:10]=1)=[O:26]

Participants

5

Reactant 3

HCID 1118Sulfuric Acid2×HCID 516892Sodium BicarbonateHCID 684251515-Benzyloxy-pyrrolo[2,3-b]pyridine-1,2-dicarboxylic acid 1-tert-butyl ester2×

Product 1

HCID 684234775-Benzyloxy-1H-pyrrolo[2,3-b]pyridine-2-carboxylic acid methyl esterYield 78%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

The suspension of 0.2 g (0.54 mmol) 5-benzyloxy-pyrrolo[2,3-b]pyridine-1,2-dicarboxylic acid 1-tert-butyl ester (intermediate G) and 30 μl of concentrated sulfuric acid in 2 ml methanol was heated under reflux. After 1.5 h another 2 ml methanol and 30 μl of concentrated sulfuric acid were added. The resulting clear solution was refluxed 3 hours and after cooling down to room temperature was poured on saturated sodium bicarbonate solution and extracted three times with ethyl acetate. The combined organic layers were washed with brine, dried over magnesium sulfate, filtered and evaporated to give 0.12 g (78%) of the product as a colorless solid.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux
  3. temperatureThe resulting clear solution was refluxed 3 hours
  4. extractionextracted three times with ethyl acetate
  5. washThe combined organic layers were washed with brine
  6. dry with materialdried over magnesium sulfate
  7. filtrationfiltered
  8. customevaporated

Sources & evidence

ORD record
ord-0513b1b52ff74182b91552955c2608c9
Source dataset
uspto-grants-2010_08
Patent number
US07786109B2

Reaction notes

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