Pyruvic Acid → 1H-Pyrrolo[2,3-b]pyridine-2,5-dicarboxylic acid, 5-Methyl ester

HRID 2250428Notes

Reaction equation

HRID 2250428 reaction equation
[CH3:1][O:2][C:3](=[O:12])[C:4]1[CH:9]=[C:8](I)[C:7]([NH2:11])=[N:6][CH:5]=1.O=[C:14]([CH3:18])[C:15]([OH:17])=[O:16].CCN(CC)CC.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>CN(C=O)C.CC([O-])=O.CC([O-])=O.[Pd+2]>[CH3:1][O:2][C:3]([C:4]1[CH:9]=[C:8]2[CH:18]=[C:14]([C:15]([OH:17])=[O:16])[NH:11][C:7]2=[N:6][CH:5]=1)=[O:12]

Participants

7

Reactant 4

HCID 1060Pyruvic AcidHCID 8471TriethylamineHCID 11776TriphenylphosphineHCID 15350913Methyl 6-amino-5-iodopyridine-3-carboxylate

Product 1

HCID 692285171H-Pyrrolo[2,3-b]pyridine-2,5-dicarboxylic acid, 5-Methyl ester

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 6228DimethylformamideSolvent

Procedure

A solution of 5.6 g 6-Amino-5-iodo-nicotinic acid methyl ester, 5.3 g 2-Oxo-propionic acid, 11.1 g NEt3, 4.2 g Triphenylphosphine and 1.1 g Pd(OAc)2 in 100 mL DMF was heated under argon to 100° C. After 10 h the reaction mixture was concentrated under reduced pressure and the residue was strirred with 250 mL water for 1 h. The precipitated product was collected by filtration and washed with water. The crude product was subjected to the next reaction step without further purification.

Workup

  1. concentrationAfter 10 h the reaction mixture was concentrated under reduced pressure
  2. filtrationThe precipitated product was collected by filtration
  3. washwashed with water
  4. customThe crude product was subjected to the next reaction step without further purification

Sources & evidence

ORD record
ord-f07b6e0ac14f400d84a4f472d1b96af8
Source dataset
uspto-grants-2008_01
Patent number
US07317027B2

Reaction notes

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