Cesium carbonate → HCID 178480727, compound

HRID 2236939Notes

Reaction equation

HRID 2236939 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.C([Si](C(C)C)(C(C)C)[N:33]1[CH:37]=[CH:36][C:35](B(O)O)=[CH:34]1)(C)C.C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C)C=O>[CH3:28][N:25]1[CH2:26][CH2:27][N:22]([C:19]2[CH:18]=[CH:17][C:16]([NH:15][CH:14]=[C:5]3[C:4]4[C:9](=[CH:10][CH:11]=[C:2]([C:35]5[CH:36]=[CH:37][NH:33][CH:34]=5)[CH:3]=4)[C:8](=[O:12])[NH:7][C:6]3=[O:13])=[CH:21][CH:20]=2)[CH2:23][CH2:24]1

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 27633031-(Triisopropylsilyl)pyrrole-3-boronic acidHCID 178480720HCID 178480720, compound

Product 1

HCID 178480727HCID 178480727, compoundYield 31.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
180 °C

Procedure

To a suspension of 6-bromo-4-{[4-(4-methyl-piperazin-1-yl)-phenylamino]-methylene}-4H-isoquinoline-1,3-dione (0.2 g, 0.45 mmol) in N,N-dimethylformamide (5 mL) is added N-triisopropylsilyl-3-pyrrole boronic acid (0.16 g, 0.54 mmol), followed by 300 μL of 2M aqueous cesium carbonate and tetrakis triphenylphosphine palladium (30 mg, 0.025 mmol). The reaction mixture is subjected to microwave heating at 180° C. for 300 seconds. The reaction mixture is then divided into 3 fractions and purified by C18 reverse phase HPLC. The pure fractions were combined and concentrated to yield 60 mg of 4-{[4-(4-methyl-piperazin-1-yl)-phenylamino]-methylene}-6-(1H-pyrrol-3-yl)-4H-isoquinoline-1,3-dione.

Workup

  1. custompurified by C18 reverse phase HPLC
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-615acb04e45843bb98edc0a0020b8374
Source dataset
uspto-grants-2010_05
Patent number
US07713994B2

Reaction notes

Loading…