Potassium Carbonate → HCID 59305023, compound

HRID 2240257Notes

Reaction equation

HRID 2240257 reaction equation
Cl[C:2]1[CH:7]=[CH:6][N:5]=[C:4]2[N:8]([CH2:15][O:16][CH2:17][CH2:18][Si:19]([CH3:22])([CH3:21])[CH3:20])[CH:9]=[C:10]([C:11]([F:14])([F:13])[F:12])[C:3]=12.[F:23][C:24]1[CH:30]=[C:29]([N+:31]([O-:33])=[O:32])[CH:28]=[CH:27][C:25]=1[NH2:26].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:23][C:24]1[CH:30]=[C:29]([N+:31]([O-:33])=[O:32])[CH:28]=[CH:27][C:25]=1[NH:26][C:2]1[C:3]2[C:10]([C:11]([F:14])([F:13])[F:12])=[CH:9][N:8]([CH2:15][O:16][CH2:17][CH2:18][Si:19]([CH3:22])([CH3:21])[CH3:20])[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 593049814-Chloro-3-(trifluoromethyl)-1-[[2-(trimethylsilyl)ethoxy]methyl]-1H-pyrrolo[2,3-b]pyridine

Product 1

HCID 59305023HCID 59305023, compound

Reagents, catalysts & solvents 2

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 6386tert-ButanolSolvent

Procedure

A solution of 170 mg (0.485 mmol) of 4-chloro-3-(trifluoromethyl)-1-{[2-(trimethylsilyl)ethoxy]-methyl}-1H-pyrrolo[2,3-b]pyridine, 91 mg (0.58 mmol) of 2-fluoro-4-nitroaniline, 31 mg (0.035 mmol) of tris(dibenzylideneacetone)dipalladium, 33 mg (0.07 mmol) of dicyclohexyl(2′,4′,6′-triisopropylbiphenyl-2-yl)phosphine and 100 mg (0.72 mmol) of potassium carbonate in 3.00 ml of degassed tert-butanol is stirred in a sealed pressure vessel at 100° C. for 3 h. After cooling to RT, the reaction mixture is filtered through kieselguhr, the kieselguhr is washed with ethyl acetate and the filtrate is freed from the solvent. The residue is purified by preparative HPLC.

Workup

  1. filtrationthe reaction mixture is filtered through kieselguhr
  2. washthe kieselguhr is washed with ethyl acetate
  3. customThe residue is purified by preparative HPLC

Sources & evidence

ORD record
ord-e07a1f1b6d7c4804ab5e798cefd779a7
Source dataset
uspto-grants-2010_05
Patent number
US07723347B2

Reaction notes

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