Potassium Carbonate → 7-Bromo-4-methoxy-α-oxo-1H-pyrrolo[2,3-c]pyridine-3-acetic acid

HRID 1783386Notes

Reaction equation

HRID 1783386 reaction equation
[Br:1][C:2]1[N:3]=[CH:4][C:5]([O:17][CH3:18])=[C:6]2[C:10]=1[NH:9][CH:8]=[C:7]2[C:11](=[O:16])[C:12]([O:14]C)=[O:13].C([O-])([O-])=O.[K+].[K+]>CO.O.O>[Br:1][C:2]1[N:3]=[CH:4][C:5]([O:17][CH3:18])=[C:6]2[C:10]=1[NH:9][CH:8]=[C:7]2[C:11](=[O:16])[C:12]([OH:14])=[O:13]

Participants

5

Reactant 2

HCID 11430Potassium CarbonateHCID 57590495Methyl 2-(7-bromo-4-methoxy-6-azaindol-3-yl)-2-oxoacetate

Product 1

HCID 575904977-Bromo-4-methoxy-α-oxo-1H-pyrrolo[2,3-c]pyridine-3-acetic acidYield 59.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 22242641Methanol--water (1/1)Solvent

Procedure

To a solution of methyl 2-(7-bromo-4-methoxy-6-azaindol-3-yl)-2-oxoacetate (0.083 g, 0.265 mmol) in MeOH—H2O (3:1, 3 mL) was added 1M aqueous K2CO3 (1.1 mL, 1.1 mmol). The mixture was stirred at room temperature for 14 h and then it was diluted with H2O (2 mL). The volatiles were removed under reduced pressure and the remaining solution was acidified to pH 1-2 using 6N HCl. The resulting suspension was cooled at 0° C., the precipitate was filtered and the filtercake was washed with H2O and then ether. After drying in vacuo, this gave the title compound (0.047 g, 59%) as a light yellow solid:

Workup

  1. customThe volatiles were removed under reduced pressure
  2. temperatureThe resulting suspension was cooled at 0° C.
  3. filtrationthe precipitate was filtered
  4. washthe filtercake was washed with H2O
  5. customAfter drying in vacuo

Sources & evidence

ORD record
ord-c4c6cf1b3e0f477bacc26e5b6b4800c6
Source dataset
uspto-grants-2009_03
Patent number
US07501419B2

Reaction notes

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