Potassium Acetate → 3-[4-(4-Methyl-piperazin-1-yl)-phenyl]-9H-dipyrido[2,3-b;4',3'-d]pyrrole-6-carboxylic acid methyl ester

HRID 1506015Notes

Reaction equation

HRID 1506015 reaction equation
[CH3:1][O:2][C:3]([C:5]1[N:13]=[CH:12][C:11]2[NH:10][C:9]3[N:14]=[CH:15][C:16](Br)=[CH:17][C:8]=3[C:7]=2[CH:6]=1)=[O:4].[CH3:19][N:20]1[CH2:25][CH2:24][N:23]([C:26]2[CH:31]=[CH:30][C:29](B(O)O)=[CH:28][CH:27]=2)[CH2:22][CH2:21]1.C([O-])(=O)C.[K+]>C(#N)C.C(=O)(O)[O-].[Na+].C(Cl)Cl.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[CH3:1][O:2][C:3]([C:5]1[N:13]=[CH:12][C:11]2[NH:10][C:9]3[N:14]=[CH:15][C:16]([C:29]4[CH:28]=[CH:27][C:26]([N:23]5[CH2:24][CH2:25][N:20]([CH3:19])[CH2:21][CH2:22]5)=[CH:31][CH:30]=4)=[CH:17][C:8]=3[C:7]=2[CH:6]=1)=[O:4]

Participants

8

Reactant 3

HCID 517044Potassium AcetateHCID 53316427(4-(4-Methylpiperazin-1-yl)phenyl)boronic acidHCID 58266719Methyl 3-bromo-9H-pyrrolo[2,3-b:5,4-c']dipyridine-6-carboxylate

Product 1

HCID 582666523-[4-(4-Methyl-piperazin-1-yl)-phenyl]-9H-dipyrido[2,3-b;4',3'-d]pyrrole-6-carboxylic acid methyl ester

Reagents, catalysts & solvents 4

HCID 178418476HCID 178418476, compoundCatalystHCID 6342AcetonitrileSolventHCID 6344DichloromethaneSolventHCID 516892Sodium BicarbonateSolvent

Procedure

3-Bromo-9H-dipyrido[2,3-b;4′,3′-d]pyrrole-6-carboxylic acid methyl ester (100 mg, 0.327 mmol), 4-(4-methylpiperazin-1-yl)phenylboronic acid, pinacol ester (104 mg, 0.343 mmol) and bis(triphenylphosphine)palladium(II) dichloride (11.5 mg, 0.016 mmol) were suspended in acetonitrile (1.8 mL) and 1N aqueous potassium acetate solution (1.8 mL) and heated under microwave irradiation at 140° C. for 30 minutes. The cooled reaction mixture was diluted with saturated sodium bicarbonate solution and DCM, and the solid removed by filtration. The layers of the resultant filtrate were separated and the aqueous phase was further extracted with DCM. The combined organic phase was dried over sodium sulfate, filtered and concentrated in vacuo. The resultant residue was purified by flash chromatography (silica, 0-20% (MeOH containing 1% triethylamine) in DCM).

Workup

  1. customThe cooled reaction mixture
  2. customthe solid removed by filtration
  3. customThe layers of the resultant filtrate were separated
  4. extractionthe aqueous phase was further extracted with DCM
  5. dry with materialThe combined organic phase was dried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe resultant residue was purified by flash chromatography (silica, 0-20% (MeOH containing 1% triethylamine) in DCM)

Sources & evidence

ORD record
ord-dc4c088aa746411a9f95bf06fdbcfb05
Source dataset
uspto-grants-2015_12
Patent number
US09216980B2

Reaction notes

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