Diethylphosphite → HCID 178476937, compound

HRID 2236743Notes

Reaction equation

HRID 2236743 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.[P:29]([O-:36])([O:33][CH2:34][CH3:35])[O:30][CH2:31][CH3:32]>CN(C)C=O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH3:28][N:25]1[CH2:24][CH2:23][N:22]([C:19]2[CH:18]=[CH:17][C:16]([NH:15]/[CH:14]=[C:5]3\[C:6](=[O:13])[NH:7][C:8](=[O:12])[C:9]4[C:4]\3=[CH:3][C:2]([P:29](=[O:36])([O:33][CH2:34][CH3:35])[O:30][CH2:31][CH3:32])=[CH:11][CH:10]=4)=[CH:21][CH:20]=2)[CH2:27][CH2:26]1

Participants

5

Reactant 2

HCID 3780918DiethylphosphiteHCID 178480719HCID 178480719, compound

Product 1

HCID 178476937HCID 178476937, compound

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
120 °C

Procedure

To a solution of (4Z)-6-bromo-4-({[4-(4-methylpiperazin-1-yl)phenyl]amino}methylene)isoquinoline-1,3(2H,4H)-dione (67 mg, 0.15 mmol) in N,N-dimethylformamide (1 mL) is added diethyl phosphite (22 μL) and tetrakis(triphenylphosphine)palladium(0) (9 mg, 8 μmol, 0.05 mol %). The mixture is heated in a 120° C. oil bath for 6 hour and then purified by reverse phase high performance liquid chromatography to give diethyl [(4Z)-4-({[4-(4-methylpiperazin-1-yl)phenyl]amino}methylene)-1,3-dioxo-1,2,3,4-tetrahydroisoquinolin-6-yl]phosphonate as its ditrifluoroacetate salt (8.8 mg, 3.1%).

Workup

  1. custompurified by reverse phase high performance liquid chromatography

Sources & evidence

ORD record
ord-4f12d900b54741e99f2132d977cd1344
Source dataset
uspto-grants-2010_05
Patent number
US07713994B2

Reaction notes

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