Cesium carbonate → HCID 178480787, compound

HRID 2236860Notes

Reaction equation

HRID 2236860 reaction equation
I[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:17]=[N:18][C:19]([N:22]2[CH2:27][CH2:26][N:25]([CH3:28])[CH2:24][CH2:23]2)=[N:20][CH:21]=1.[O:29]1[CH:33]=[CH:32][C:31](B(O)O)=[CH:30]1.C(=O)([O-])[O-].[Cs+].[Cs+].P(C(C)(C)C)(C(C)(C)C)C(C)(C)C>C(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].CN(C)C=O>[O:29]1[CH:33]=[CH:32][C:31]([C:2]2[CH:3]=[C:4]3[C:9](=[CH:10][CH:11]=2)[C:8](=[O:12])[NH:7][C:6](=[O:13])/[C:5]/3=[CH:14]\[NH:15][C:16]2[CH:21]=[N:20][C:19]([N:22]3[CH2:27][CH2:26][N:25]([CH3:28])[CH2:24][CH2:23]3)=[N:18][CH:17]=2)=[CH:30]1

Participants

8

Reactant 4

HCID 10796Cesium carbonateHCID 83681Tris(1,1-dimethylethyl)phosphineHCID 2734358Furan-3-boronic acidHCID 178480789HCID 178480789, compound

Product 1

HCID 178480787HCID 178480787, compoundYield 55.8%

Reagents, catalysts & solvents 3

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

(4Z)-6-Iodo-4-({[2-(4-methylpiperazin-1-yl)pyrimidin-5-yl]amino}methylene)isoquinoline-1,3(2H,4H)-dione (73.5 mg, 0.15 mmol) is mixed with 3-furanboronic acid (33 mg, 0.3 mmol), Pd2(dba)3 (20.6 mg, 0.022 mmol), and cesium carbonate (98 mg, 0.3 mmol). After the solids were degassed, N,N-dimethylformamide (1.05 mL) and P(t-Bu)3 (9.1 mg, 0.045 mmol) were added. The mixture is heated at 100 C for 55 min, diluted with methylene chloride, and filtered. The filtrate is evaporated to dryness and purified by column chromatography to yield 36 mg (55%) of the title compound as a yellow solid. MS (ESI) m/z 431 (M+H)+1

Workup

  1. customAfter the solids were degassed
  2. temperatureThe mixture is heated at 100 C for 55 min
  3. filtrationfiltered
  4. customThe filtrate is evaporated to dryness
  5. custompurified by column chromatography

Sources & evidence

ORD record
ord-2559ecd670bf4840a07673756f7da80d
Source dataset
uspto-grants-2010_05
Patent number
US07713994B2

Reaction notes

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