Potassium Carbonate → HCID 59304987, compound

HRID 2240223Notes

Reaction equation

HRID 2240223 reaction equation
Cl[C:2]1[CH:7]=[CH:6][N:5]=[C:4]2[NH:8][CH:9]=[C:10]([CH3:11])[C:3]=12.[F:12][C:13]1[CH:19]=[C:18]([N+:20]([O-:22])=[O:21])[CH:17]=[CH:16][C:14]=1[NH2:15].C1(P(C2CCCCC2)C2C=CC=CC=2C2C(C(C)C)=CC(C(C)C)=CC=2C(C)C)CCCCC1.C(=O)([O-])[O-].[K+].[K+]>C(O)(C)(C)C.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[F:12][C:13]1[CH:19]=[C:18]([N+:20]([O-:22])=[O:21])[CH:17]=[CH:16][C:14]=1[NH:15][C:2]1[C:3]2[C:10]([CH3:11])=[CH:9][NH:8][C:4]=2[N:5]=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 11430Potassium CarbonateHCID 1012542-Fluoro-4-nitroanilineHCID 111557942-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenylHCID 179793234-Chloro-3-methyl-1H-pyrrolo[2,3-b]pyridine

Product 1

HCID 59304987HCID 59304987, compound

Reagents, catalysts & solvents 2

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 6386tert-ButanolSolvent

Procedure

A solution of 8 mg (50 μmol) of 4-chloro-3-methyl-1H-pyrrolo[2,3-b]pyridine, 9 mg (60 μmol) of 2-fluoro-4-nitroaniline, 4 mg (5 mmol) of tris(dibenzylideneacetone)dipalladium and 5 mg (10 μmol) of dicyclohexyl(2′,4′,6′-triisopropylbiphenyl-2-yl)phosphine and 10 mg (70 μmol) of potassium carbonate in 1.00 ml of degassed tert-butanol is stirred at 100° C. in a sealed pressure vessel for 3 h. After cooling to RT, the mixture is filtered through Celite, the Celite is washed with methanol and the filtrates are concentrated under reduced pressure. The residue is purified by column chromatography on silica gel (mobile phase: cyclohexane/ethyl acetate 1:1).

Workup

  1. filtrationthe mixture is filtered through Celite
  2. washthe Celite is washed with methanol
  3. concentrationthe filtrates are concentrated under reduced pressure
  4. customThe residue is purified by column chromatography on silica gel (mobile phase: cyclohexane/ethyl acetate 1:1)

Sources & evidence

ORD record
ord-8303336c511a4392b4b5a38f8007ad03
Source dataset
uspto-grants-2010_05
Patent number
US07723347B2

Reaction notes

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