HCID 22499174, compound → HCID 22499212, compound

HRID 244773Notes

Reaction equation

HRID 244773 reaction equation
Br[C:2]1[C:11]([CH3:12])=[CH:10][C:9]([O:13][CH2:14][O:15][CH3:16])=[C:8]2[C:3]=1[CH:4]=[CH:5][C:6](=[O:17])[NH:7]2.[CH2:18](C([Sn])=C(CCCC)CCCC)[CH2:19]CC>CN(C)C=O.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.Cl[Pd]Cl>[CH3:16][O:15][CH2:14][O:13][C:9]1[CH:10]=[C:11]([CH3:12])[C:2]([CH:18]=[CH2:19])=[C:3]2[C:8]=1[NH:7][C:6](=[O:17])[CH:5]=[CH:4]2

Participants

5

Reactant 2

HCID 22499174HCID 22499174, compoundHCID 53438229Tri(butyl)vinyltin

Product 1

HCID 22499212HCID 22499212, compound

Reagents, catalysts & solvents 2

HCID 6102075Dichlorobis(triphenylphosphine)palladiumCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

Bis-(triphenylphosphine)palladium (II) chloride (98 mg) is added to a solution of 5-bromo-8-methoxymethoxy-6-methyl-1H-quinolin-2-one (410 mg) and tributylvinyltin (603 μL) in dimethylformamide (14 mL) at room temperature. The reaction mixture is heated for 24 hours at 90° C., evaporated and purified by flash column chromatography on silica gel, eluting with 2% methanol in dichloromethane.

Workup

  1. customevaporated
  2. custompurified by flash column chromatography on silica gel
  3. washeluting with 2% methanol in dichloromethane

Sources & evidence

ORD record
ord-d7556c0eacc8449386c58d9d71f30a75
Source dataset
uspto-grants-2014_02
Patent number
US08658673B2

Reaction notes

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