Cesium carbonate → HCID 178462680, compound

HRID 2236821Notes

Reaction equation

HRID 2236821 reaction equation
[CH2:1]([N:3]1[CH2:8][CH2:7][N:6]([C:9]2[N:14]=[CH:13][C:12]([NH:15]/[CH:16]=[C:17]3\[C:18](=[O:29])[NH:19][C:20](=[O:28])[C:21]4[C:26]\3=[CH:25][C:24](I)=[CH:23][CH:22]=4)=[CH:11][CH:10]=2)[CH2:5][CH2:4]1)[CH3:2].[O:30]1[CH:34]=[CH:33][C:32](B(O)O)=[CH:31]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>[CH2:1]([N:3]1[CH2:8][CH2:7][N:6]([C:9]2[N:14]=[CH:13][C:12]([NH:15]/[CH:16]=[C:17]3\[C:18](=[O:29])[NH:19][C:20](=[O:28])[C:21]4[C:26]\3=[CH:25][C:24]([C:32]3[CH:33]=[CH:34][O:30][CH:31]=3)=[CH:23][CH:22]=4)=[CH:11][CH:10]=2)[CH2:5][CH2:4]1)[CH3:2]

Participants

8

Reactant 4

HCID 10796Cesium carbonateHCID 83681Tris(1,1-dimethylethyl)phosphineHCID 2734358Furan-3-boronic acidHCID 178462684HCID 178462684, compound

Product 1

HCID 178462680HCID 178462680, compoundYield 67.6%

Reagents, catalysts & solvents 3

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

(4Z)-4-({[6-(4-Ethylpiperazin-1-yl)pyridin-3-yl]amino}methylene)-6-iodoisoquinoline-1,3(2H,4H)-dione (50.3 mg, 0.1 mmol) is mixed with 3-furanboronic acid (22 mg, 0.2 mmol), Pd2(dba)3 (13.7 mg, 0.015 mmol), and cesium carbonate (65 mg, 0.2 mmol). After the solids were degassed, N,N-dimethylformamide (0.7 mL) and P(t-Bu)3 (6 mg, 0.03 mmol) were added. The mixture is heated at 100 C for 10 min, diluted with methylene chloride, and filtered. The filtrate is evaporated to dryness and purified by column chromatography to yield 30 mg (67%) of the title compound as an orange solid. MS (ESI) m/z 444 (M+H)+1

Workup

  1. customAfter the solids were degassed
  2. temperatureThe mixture is heated at 100 C for 10 min
  3. filtrationfiltered
  4. customThe filtrate is evaporated to dryness
  5. custompurified by column chromatography

Sources & evidence

ORD record
ord-5e3015501f1d4e8292f87748476db0de
Source dataset
uspto-grants-2010_05
Patent number
US07713994B2

Reaction notes

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