Methane → ethyl 3-(4-aminophenyl)-1H-pyrrolo[2,3-c]pyridine-2-carboxylate

HRID 550891

Reaction equation

HRID 550891 reaction equation
Br[C:2]1[C:10]2[C:5](=[CH:6][N:7]=[CH:8][CH:9]=2)[NH:4][C:3]=1[C:11]([O:13][CH2:14][CH3:15])=[O:12].Cl.[NH2:17][C:18]1[CH:23]=[CH:22][C:21](B(O)O)=[CH:20][CH:19]=1.[F-].[K+].C>O1CCOCC1.O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C(N(CC)CC)C>[NH2:17][C:18]1[CH:23]=[CH:22][C:21]([C:2]2[C:10]3[C:5](=[CH:6][N:7]=[CH:8][CH:9]=3)[NH:4][C:3]=2[C:11]([O:13][CH2:14][CH3:15])=[O:12])=[CH:20][CH:19]=1

Participants

9

Reactant 4

HCID 297MethaneHCID 522689Potassium FluorideHCID 2734614(4-Aminophenyl)boronic acid hydrochlorideHCID 57445353ethyl 3-bromo-1H-pyrrolo[2,3-c]pyridine-2-carboxylate

Product 1

HCID 57445352ethyl 3-(4-aminophenyl)-1H-pyrrolo[2,3-c]pyridine-2-carboxylateYield 57.4%

Reagents, catalysts & solvents 4

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolventHCID 8471TriethylamineSolventHCID 312751,4-DioxaneSolvent

Procedure

To a solution of 1 g of ethyl 3-bromo-1H-pyrrolo[2,3-c]pyridine-2-carboxylate in 100 mL of dioxane are added 773 mg of 4-aminophenylboronic acid hydrochloride and 1.1 g of potassium fluoride in 9 mL of water. The reaction mixture is stirred under an argon atmosphere for 15 minutes. 425 mg of tetrakis(triphenylphosphine)palladium(0) and 630 μL of triethylamine are added. The reaction mixture is stirred for 17 hours at reflux. After treating with carbon black and then filtering through Celite®, the filtrate is concentrated under reduced pressure. The residue is purified by flash chromatography on a column of silica (60; 35-70 μM), eluting with a mixture of dichloromethane, methanol and acetonitrile (90/5/5 by volume). 600 mg of ethyl 3-(4-aminophenyl)-1H-pyrrolo[2,3-c]pyridine-2-carboxylate are obtained, the characteristics of which are as follows:

Workup

  1. stirringThe reaction mixture is stirred for 17 hours
  2. temperatureat reflux
  3. filtrationfiltering through Celite®
  4. concentrationthe filtrate is concentrated under reduced pressure
  5. customThe residue is purified by flash chromatography on a column of silica (60; 35-70 μM)
  6. washeluting with a mixture of dichloromethane, methanol and acetonitrile (90/5/5 by volume)

Sources & evidence

ORD record
ord-cb85bc5963f54265acc359ec33f26a0a
Source dataset
uspto-grants-2011_05
Patent number
US07947706B2

Linked notes

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