Cesium carbonate → HCID 178480724, compound

HRID 2236751Notes

Reaction equation

HRID 2236751 reaction equation
Br[C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8](=[O:12])[NH:7][C:6](=[O:13])[C:5]2=[CH:14][NH:15][C:16]1[CH:21]=[CH:20][C:19]([N:22]2[CH2:27][CH2:26][N:25]([CH3:28])[CH2:24][CH2:23]2)=[CH:18][CH:17]=1.[F:29][C:30]([F:42])([F:41])[O:31][C:32]1[CH:37]=[CH:36][C:35](B(O)O)=[CH:34][CH:33]=1.C(P(C(C)(C)C)C(C)(C)C)(C)(C)C.C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C=O)C.C(Cl)(Cl)Cl.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]>[CH3:28][N:25]1[CH2:24][CH2:23][N:22]([C:19]2[CH:20]=[CH:21][C:16]([NH:15]/[CH:14]=[C:5]3\[C:6](=[O:13])[NH:7][C:8](=[O:12])[C:9]4[C:4]\3=[CH:3][C:2]([C:35]3[CH:34]=[CH:33][C:32]([O:31][C:30]([F:29])([F:41])[F:42])=[CH:37][CH:36]=3)=[CH:11][CH:10]=4)=[CH:17][CH:18]=2)[CH2:27][CH2:26]1

Participants

8

Reactant 4

HCID 10796Cesium carbonateHCID 83681Tris(1,1-dimethylethyl)phosphineHCID 27343864-(Trifluoromethoxy)phenylboronic acidHCID 178480720HCID 178480720, compound

Product 1

HCID 178480724HCID 178480724, compoundYield 72%

Reagents, catalysts & solvents 3

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 6212ChloroformSolventHCID 6228DimethylformamideSolvent

Procedure

An amount of 6-bromo-4-{[4-(4-methyl-piperazin-1-yl)-phenylamino]-methylene}-4H-isoquinoline-1,3-dione (0.1 g, 0.2267 mmol) in 1 mL of N,N′-dimethylformamide is added to 4-(trifluoromethoxy)phenylboronic acid (0.07 g, 0.34 mmol), 0.032 g (0.034 mmol) of tris(dibenzylideneacetone)dipalladium(0), tri(t-butyl)phosphine (0.014 g, 0.068 mmol) and cesium carbonate (0.148 g, 0.4534 mmol). The reaction mixture is stirred at 130 oC under N2 for 15 min. Mass spectroscopy suggested the completion of the reaction. The mixture is diluted with chloroform and filtered through Celite. The filtrate is evaporated to dryness and purified by column chromatography using 5% methanol/methylene chloride as eluent to yield 85 mg (72% yield) of the title compound as orange solid. MS (ESI) m/z 523.2 (M+H)+1.

Workup

  1. customthe completion of the reaction
  2. filtrationfiltered through Celite
  3. customThe filtrate is evaporated to dryness
  4. custompurified by column chromatography

Sources & evidence

ORD record
ord-d7ffa9c1d5bf40d8ac670d0dfc06df7e
Source dataset
uspto-grants-2010_05
Patent number
US07713994B2

Reaction notes

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