Sodium Carbonate → HCID 57445355, compound

HRID 550898Notes

Reaction equation

HRID 550898 reaction equation
Br[C:2]1[C:10]2[C:5](=[N:6][CH:7]=[CH:8][CH:9]=2)[NH:4][C:3]=1[C:11]([O:13][CH3:14])=[O:12].Cl.[NH2:16][C:17]1[CH:22]=[CH:21][C:20](B(O)O)=[CH:19][CH:18]=1.[Cl-].[Li+].C(=O)([O-])[O-].[Na+].[Na+]>C1(C)C=CC=CC=1.CO.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.O.C(N(CC)CC)C>[NH2:16][C:17]1[CH:22]=[CH:21][C:20]([C:2]2[C:10]3[C:5](=[N:6][CH:7]=[CH:8][CH:9]=3)[NH:4][C:3]=2[C:11]([O:13][CH3:14])=[O:12])=[CH:19][CH:18]=1

Participants

10

Reactant 4

HCID 10340Sodium CarbonateHCID 433294Lithium ChlorideHCID 2734614(4-Aminophenyl)boronic acid hydrochlorideHCID 44608103HCID 44608103, compound

Product 1

HCID 57445355HCID 57445355, compoundYield 59.6%

Reagents, catalysts & solvents 5

HCID 178418397HCID 178418397, compoundCatalystHCID 887MethanolSolventHCID 962WaterSolventHCID 1140TolueneSolventHCID 8471TriethylamineSolvent

Procedure

To a solution of 0.64 g of methyl 3-bromo-1H-pyrrolo[2,3-b]pyridine-2-carboxylate in 50 mL of toluene and 50 ml of methanol are added 1.08 g of 4-aminophenylboronic acid hydrochloride and 0.9 ml of triethylamine. The reaction mixture is then stirred under an argon atmosphere for 15 minutes. 144 mg of tetrakis(triphenylphosphine)palladium(0), 0.3 g of lithium chloride, 0.66 g of sodium carbonate and 7.5 mL of distilled water are successively added. The reaction mixture is stirred for 8 hours at reflux. After filtering through Celite®, the filtrate is concentrated under reduced pressure. The residue is purified by column chromatography on silica, eluting with a mixture of ethyl acetate and cyclohexane (7/3 by volume). 400 mg of methyl 3-(4-aminophenyl)-1H-pyrrolo[2,3-b]pyridine-2-carboxylate are obtained in the form of a yellow solid, the characteristics of which are as follows:

Workup

  1. stirringThe reaction mixture is stirred for 8 hours
  2. temperatureat reflux
  3. filtrationAfter filtering through Celite®
  4. concentrationthe filtrate is concentrated under reduced pressure
  5. customThe residue is purified by column chromatography on silica
  6. washeluting with a mixture of ethyl acetate and cyclohexane (7/3 by volume)

Sources & evidence

ORD record
ord-df7a5b00c431429c95e13c81ab2d0451
Source dataset
uspto-grants-2011_05
Patent number
US07947706B2

Reaction notes

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