Potassium Carbonate → ethyl 3-(4-nitrophenyl)-1H-pyrrolo[3,2-b]pyridine-2-carboxylate

HRID 230546Notes

Reaction equation

HRID 230546 reaction equation
C(=O)([O-])[O-].[K+].[K+].Br[C:8]1[C:12]2=[N:13][CH:14]=[CH:15][CH:16]=[C:11]2[NH:10][C:9]=1[C:17]([O:19][CH2:20][CH3:21])=[O:18].[N+:22]([C:25]1[CH:30]=[CH:29][C:28](B(O)O)=[CH:27][CH:26]=1)([O-:24])=[O:23]>O1CCOCC1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Pd]>[N+:22]([C:25]1[CH:30]=[CH:29][C:28]([C:8]2[C:12]3=[N:13][CH:14]=[CH:15][CH:16]=[C:11]3[NH:10][C:9]=2[C:17]([O:19][CH2:20][CH3:21])=[O:18])=[CH:27][CH:26]=1)([O-:24])=[O:23]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 27735524-Nitrophenylboronic acidHCID 577628443-Bromo-1H-pyrrolo[3,2-B]pyridine-2-carboxylic acid ethyl ester

Product 1

HCID 57762837ethyl 3-(4-nitrophenyl)-1H-pyrrolo[3,2-b]pyridine-2-carboxylateYield 22.5%

Reagents, catalysts & solvents 2

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 312751,4-DioxaneSolvent

Procedure

3 g of potassium carbonate and 0.8 g of palladium tetrakis(triphenylphosphine) are added to a solution of 2 g of ethyl 3-bromo-1H-pyrrolo[3,2-b]pyridine-2-carboxylate and 1.5 g of 4-nitrophenylboronic acid in 50 ml of dioxane. The mixture is refluxed for 20 hours, and then filtered. The filtrate is concentrated under reduced pressure and the residue is purified by chromatography on a silica column, elution being carried out with a mixture of cyclohexane and ethyl acetate (50/50 by volume), to give 0.52 g of ethyl 3-(4-nitrophenyl)-1H-pyrrolo[3,2-b]pyridine-2-carboxylate, the characteristics of which are as follows:

Workup

  1. temperatureThe mixture is refluxed for 20 hours
  2. filtrationfiltered
  3. concentrationThe filtrate is concentrated under reduced pressure
  4. customthe residue is purified by chromatography on a silica column, elution
  5. additionbeing carried out with a mixture of cyclohexane and ethyl acetate (50/50 by volume)

Sources & evidence

ORD record
ord-570c63974fce4ee6b9052ea3d84d19d1
Source dataset
uspto-grants-2009_07
Patent number
US07566736B2

Reaction notes

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