Pyruvic Acid → 1H-Pyrrolo[3,2-b]pyridine-2-carboxylic acid

HRID 2250432Notes

Reaction equation

HRID 2250432 reaction equation
O=[C:2]([CH3:6])[C:3]([OH:5])=[O:4].C(N(CC)CC)C.Br[C:15]1[C:20]([NH2:21])=[CH:19][CH:18]=[CH:17][N:16]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>CN(C)C=O.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[NH:21]1[C:20]2[C:15](=[N:16][CH:17]=[CH:18][CH:19]=2)[CH:6]=[C:2]1[C:3]([OH:5])=[O:4]

Participants

7

Reactant 4

HCID 1060Pyruvic AcidHCID 8471TriethylamineHCID 11776TriphenylphosphineHCID 6428163-Amino-2-bromopyridine

Product 1

HCID 226126701H-Pyrrolo[3,2-b]pyridine-2-carboxylic acid

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

1.22 mL 2-oxo-propionic acid, 0.26 g palladium acetate and 3.20 mL triethylamine were added to a solution of 1.00 g 2-bromo-pyridin-3-yl amine and 1.21 g triphenyl-phosphine in 10 mL N,N-dimethylformamide. The reaction mixture was stirred for 4 hours at 100° C. After removal of the solvent under reduced pressure, the residue was purified by column chromatography on silica gel with dichloromethane/methanol as eluent. Yield: 260 mg MS(ES+): m/e=163.

Workup

  1. customAfter removal of the solvent under reduced pressure
  2. customthe residue was purified by column chromatography on silica gel with dichloromethane/methanol as eluent

Sources & evidence

ORD record
ord-b10c824216a5428b99a01fe117853b3d
Source dataset
uspto-grants-2008_01
Patent number
US07317027B2

Reaction notes

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