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

HRID 1157754Notes

Reaction equation

HRID 1157754 reaction equation
[F:1][C:2]1[CH:7]=[N:6][C:5]([NH2:8])=[C:4]2[NH:9][CH:10]=[CH:11][C:3]=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>[NH2:8][C:5]1[N:6]=[CH:7][C:2]([F:1])=[C:3]2[C:11]([C:26](=[O:31])[C:27]([OH:29])=[O:28])=[CH:10][NH:9][C:4]=12

Participants

6

Reactant 4

HCID 79846Methyl chloroglyoxylateHCID 6451240Aluminum(III) ChlorideHCID 159870184-fluoro-1H-pyrrolo[2,3-c]pyridin-7-amineHCID 17821953Ethylmethylimidazolium chloride

Product 1

HCID 595111932-(7-amino-4-fluoro-1H-pyrrolo[2,3-c]pyridin-3-yl)-2-oxoacetic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

4-fluoro-1H-pyrrolo[2,3-c]pyridin-7-amine (2.26 g, 15 mmol) was added to a mixture of AlCl3 (12.0 g, 90.0 mmol) and ethylmethylimidazolium chloride (4.38 g, 30.0 mmol). Methyl chlorooxoacetate (3.6 mL, 30.0 mmol) was added slowly to the above solution and the mixture was stirred at rt 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 suspended in DMF. TEA (7 mL) was added and the mixture was stirred at rt for 1 h. Solvent was removed in vacuum. Chloroform (50 mL) was added and the solid was collected by filtration to afford 2-(7-amino-4-fluoro-1H-pyrrolo[2,3-c]pyridin-3-yl)-2-oxoacetic acid as a bright yellow solid (2.3 g, 90% pure). LCMS: m/e 238 (M+H)+, ret time 0.96 min (method 3).

Workup

  1. customReaction flask
  2. customwas placed in an ice bath
  3. customformed
  4. filtrationThe solid was collected by filtration
  5. additionTEA (7 mL) was added
  6. stirringthe mixture was stirred at rt for 1 h
  7. customSolvent was removed in vacuum
  8. additionChloroform (50 mL) was added
  9. filtrationthe solid was collected by filtration

Sources & evidence

ORD record
ord-4bc8b57a51444c18a5aa287d8dacdb7c
Source dataset
uspto-grants-2010_10
Patent number
US07807676B2

Reaction notes

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