Cesium carbonate → 6-(furan-3-yl)-7-methoxy-4-[[4-(4-methylpiperazin-1-yl)anilino]methylidene]isoquinoline-1,3-dione

HRID 2236718Notes

Reaction equation

HRID 2236718 reaction equation
Br[C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[O:12][CH3:13])[C:8](=[O:14])[NH:7][C:6](=[O:15])[C:5]2=[CH:16][NH:17][C:18]1[CH:23]=[CH:22][C:21]([N:24]2[CH2:29][CH2:28][N:27]([CH3:30])[CH2:26][CH2:25]2)=[CH:20][CH:19]=1.[O:31]1[CH:35]=[CH:34][C:33](B(O)O)=[CH:32]1.C(P(C(C)(C)C)C(C)(C)C)(C)(C)C.C(=O)([O-])[O-].[Cs+].[Cs+]>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.C(Cl)(Cl)Cl.[Pd].[Pd].CN(C)C=O>[O:31]1[CH:35]=[CH:34][C:33]([C:2]2[CH:3]=[C:4]3[C:9](=[CH:10][C:11]=2[O:12][CH3:13])[C:8](=[O:14])[NH:7][C:6](=[O:15])[C:5]3=[CH:16][NH:17][C:18]2[CH:23]=[CH:22][C:21]([N:24]3[CH2:25][CH2:26][N:27]([CH3:30])[CH2:28][CH2:29]3)=[CH:20][CH:19]=2)=[CH:32]1

Participants

7

Reactant 4

HCID 10796Cesium carbonateHCID 83681Tris(1,1-dimethylethyl)phosphineHCID 2734358Furan-3-boronic acidHCID 178486408HCID 178486408, compound

Product 1

HCID 1784864126-(furan-3-yl)-7-methoxy-4-[[4-(4-methylpiperazin-1-yl)anilino]methylidene]isoquinoline-1,3-dioneYield 68.9%

Reagents, catalysts & solvents 2

HCID 11029508Palladium, tris[mu-[(1,2-eta:4,5-eta)-(1E,4E)-1,5-diphenyl-1,4-pentadien-3-one]]di-, compd. with trichloromethane (1:1)CatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
110 °C

Procedure

A mixture of 6-Bromo-7-methoxy-4-{[4-(4-methyl-piperazin-1-yl)-phenylamino]-methylene}-4H-isoquinoline-1,3-dione (241 mg, 0.51 mmole), N,N-dimethylformamide (2 mL), furan-3-boronic acid (143 mg, 1.28 mmole), tris(dibenzylideneacetone)dipalladium(0)-chloroform adduct (64 mg, 0.062 mmole), tri(t-butyl)phosphine (25 mg, 0.124 mmole) and cesium carbonate (334 mg, 1.02 mmole) is stirred and heated at 110° C. for one hour, cooled in the refrigerator. The reaction mixture is evaporated to dryness, taken up in 5% methanol in chlororform and passed through a short pad of Florisil eluting with 5% methanol in chloroform. The eluate is evaporated in vacuo and treated with acetonitrile, filtered and dried to give a brown solid 161 mg (68%), mp 198-220° C.; MS (ESI): m/z 459.2, 461.2 (M+H).

Workup

  1. temperaturecooled in the refrigerator
  2. customThe reaction mixture is evaporated to dryness
  3. customThe eluate is evaporated in vacuo
  4. additiontreated with acetonitrile
  5. filtrationfiltered
  6. customdried

Sources & evidence

ORD record
ord-0f22514c95c6400d88b27d333f50f96a
Source dataset
uspto-grants-2010_05
Patent number
US07713994B2

Reaction notes

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