Pyruvic Acid → 6-Chloro-1H-pyrrolo(2,3-b)pyridine-2-carboxylic acid

HRID 1521698

Reaction equation

HRID 1521698 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([NH2:8])[C:5](I)=[CH:4][CH:3]=1.C1N2CCN(CC2)C1.[C:18]([OH:23])(=[O:22])[C:19]([CH3:21])=O>CN(C=O)C.CC([O-])=O.CC([O-])=O.[Pd+2]>[Cl:1][C:2]1[N:7]=[C:6]2[NH:8][C:19]([C:18]([OH:23])=[O:22])=[CH:21][C:5]2=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 1060Pyruvic AcidHCID 9237DabcoHCID 454803652-Amino-6-chloro-3-iodopyridine

Product 1

HCID 219765806-Chloro-1H-pyrrolo(2,3-b)pyridine-2-carboxylic acidYield 194.8%

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
110 °C

Procedure

To a solution of 6-chloro-3-iodopyridin-2-amine (24 g, 94 mmol) in DMF is added DABCO (32 g, 283 mmol) and pyruvic acid (20 mL, 283 mmol). The mixture is degassed by bubbling argon gas through the mixture for 20 min. Pd(OAc)2 (1 g, 4.7 mmol) is added and the mixture is again degassed. The reaction mixture is heated at 110° C. for 3 h, and the solvent is evaporated to afford the title compound as a viscous liquid (36 g, >99%) which is used in the next step without purification.

Workup

  1. customThe mixture is degassed
  2. customby bubbling argon gas through the mixture for 20 min
  3. customthe mixture is again degassed
  4. customthe solvent is evaporated

Sources & evidence

ORD record
ord-99ed89870ee64cec90aa651c6f43d132
Source dataset
uspto-grants-2015_07
Patent number
US09073926B2

Linked notes

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