Sodium Carbonate → HCID 178461503, compound

HRID 2236703Notes

Reaction equation

HRID 2236703 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][C@H:26]([CH3:28])[N:25]([CH3:29])[C@H:24]([CH3:30])[CH2:23]2)=[CH:18][CH:17]=1.[O:31]1[CH:35]=[CH:34][C:33](B(O)O)=[CH:32]1.C(P(C(C)(C)C)C1C=CC=CC=1C1C=CC=CC=1)(C)(C)C.C(=O)([O-])[O-].[Na+].[Na+]>CN(C=O)C>[O:31]1[CH:35]=[CH:34][C:33]([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]=[CH:20][C:19]([N:22]3[CH2:27][C@H:26]([CH3:28])[N:25]([CH3:29])[C@H:24]([CH3:30])[CH2:23]3)=[CH:18][CH:17]=2)=[CH:32]1

Participants

6

Reactant 4

HCID 10340Sodium CarbonateHCID 27342152-(Di-tert-butylphosphino)biphenylHCID 2734358Furan-3-boronic acidHCID 178461500HCID 178461500, compound

Product 1

HCID 178461503HCID 178461503, compoundYield 43.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

An amount of 0.15 g (0.32 mmol) of (4Z)-6-bromo-4-[({4-[(3R,5S)-3,4,5-trimethylpiperazin-1-yl]phenyl}amino)-methylene]-isoquinoline-1,3(2H,4H)-dione in 2 mL of DMF is added 0.076 g (0.64 mmol) of 3-furanboronic acid, 0.02 g (0.017 mmol) of tris(dibenzyldeneaacetone)-dipalladium(0), 0.02 g (0.064 mmol) of 2-(di-t-butyl-phosphino)-biphenyl, and 0.072 g (0.64 mmol) of sodium carbonate. The reaction mixture is stirred at 100 oC under N2 for 2 h. Mass spectroscopy suggested the completion of reaction. Solids were removed by filtration, and solvent is subsequently evaporated under high-pressure vacuum to brown solid. The residue is purified using silica gel chromatography (using 5% MeOH/CHCl3 as eluent), 0.064 mg (43.8% yield) of yellow solid is obtained: mp 204-205 oC; MS (ESI) m/z 457.2 (M+H)+1

Workup

  1. customthe completion of reaction
  2. customSolids were removed by filtration, and solvent
  3. customis subsequently evaporated under high-pressure vacuum to brown solid
  4. customThe residue is purified

Sources & evidence

ORD record
ord-a25df663ed8f420891c702e41e2c27c9
Source dataset
uspto-grants-2010_05
Patent number
US07713994B2

Reaction notes

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