Methyl chloroglyoxylate → 2-(7-bromo-4-fluoro-1H-pyrrolo[2,3-c]pyridin-3-yl)-2-oxoacetic acid

HRID 1157745Notes

Reaction equation

HRID 1157745 reaction equation
[Br:1][C:2]1[N:3]=[CH:4][C:5]([F:11])=[C:6]2[CH:10]=[CH:9][NH:8][C:7]=12.[Al+3].[Cl-].[Cl-].[Cl-].[Cl-].C(C1NC=C[N+]=1C)C.Cl[C:26](=[O:31])[C:27]([O:29]C)=[O:28]>O>[Br:1][C:2]1[N:3]=[CH:4][C:5]([F:11])=[C:6]2[C:10]([C:26](=[O:31])[C:27]([OH:29])=[O:28])=[CH:9][NH:8][C:7]=12

Participants

6

Reactant 4

HCID 79846Methyl chloroglyoxylateHCID 6451240Aluminum(III) ChlorideHCID 159870217-Bromo-4-fluoro-1H-pyrrolo[2,3-C]pyridineHCID 17821953Ethylmethylimidazolium chloride

Product 1

HCID 207912392-(7-bromo-4-fluoro-1H-pyrrolo[2,3-c]pyridin-3-yl)-2-oxoacetic acidYield 92%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

7-bromo-4-fluoro-1H-pyrrolo[2,3-c]pyridine (2.0 g, 9.3 mmol) was added to a mixture of AlCl3 (7.5 g, 55.8 mmol) and ethylmethylimidazolium chloride (2.7 g, 18.6 mmol). Methyl chlorooxoacetate (2.1 mL, 18.6 mmol) was added slowly to the above solution and the mixture was stirred at room temperature for 3 h. Reaction flask was placed in an ice bath and water was slowly added until a white precipitate formed. The solid was collected by filtration and washed with water to afford 2-(7-bromo-4-fluoro-1H-pyrrolo[2,3-c]pyridin-3-yl)-2-oxoacetic acid (2.4 g, 92%). LCMS: m/e 287 (M+H)+, ret time 0.91 min (method 1).

Workup

  1. customReaction flask
  2. customwas placed in an ice bath
  3. customformed
  4. filtrationThe solid was collected by filtration
  5. washwashed with water

Sources & evidence

ORD record
ord-b1c060cd7dab42e9b9dd2b19cfce0c79
Source dataset
uspto-grants-2010_10
Patent number
US07807676B2

Reaction notes

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