Iodide Ion → 6-(4-Chloro-benzoyl)-1-methyl-4-(3-trimethylsilanylethynyl-phenyl)-1H-quinolin-2-one

HRID 479575Notes

Reaction equation

HRID 479575 reaction equation
[Cl:1][C:2]1[CH:28]=[CH:27][C:5]([C:6]([C:8]2[CH:9]=[C:10]3[C:15](=[CH:16][CH:17]=2)[N:14]([CH3:18])[C:13](=[O:19])[CH:12]=[C:11]3[C:20]2[CH:25]=[CH:24][CH:23]=[C:22](I)[CH:21]=2)=[O:7])=[CH:4][CH:3]=1.[CH3:29][Si:30]([C:33]#[CH:34])([CH3:32])[CH3:31].[Al].[I-]>C(NCC)C.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.[Cu].CN(C)C=O>[Cl:1][C:2]1[CH:28]=[CH:27][C:5]([C:6]([C:8]2[CH:9]=[C:10]3[C:15](=[CH:16][CH:17]=2)[N:14]([CH3:18])[C:13](=[O:19])[CH:12]=[C:11]3[C:20]2[CH:25]=[CH:24][CH:23]=[C:22]([C:34]#[C:33][Si:30]([CH3:32])([CH3:31])[CH3:29])[CH:21]=2)=[O:7])=[CH:4][CH:3]=1

Participants

9

Reactant 4

HCID 30165Iodide IonHCID 66111TrimethylsilylacetyleneHCID 5359268AluminumHCID 154896306-(4-Chloro-benzoyl)4-(3-iodo-phenyl)-1-methyl-1H-quinolin-2-one

Product 1

HCID 154896316-(4-Chloro-benzoyl)-1-methyl-4-(3-trimethylsilanylethynyl-phenyl)-1H-quinolin-2-one

Reagents, catalysts & solvents 4

HCID 23978CopperCatalystHCID 178418476HCID 178418476, compoundCatalystHCID 6228DimethylformamideSolventHCID 8021DiethylamineSolvent

Procedure

6-(4-Chloro-benzoyl)-4-(3-iodo-phenyl)-1-methyl-1H-quinolin-2-one (9.98 g, 20.0 mMol) was suspended in diethylamine (300 mL). To this solution was added 50 mL of anhydrous N,N-dimethylformamide (DMF), (trimethylsilyl)acetylene (8.5 mL) and bis(triphenylphosphine)-palladium(II) chloride (1.40 g, 2.00 mMol). The flask was covered with aluminum foil and then copper(l) iodide (780 mg, 4.09 mMol) was added causing the reaction mixture to exotherm. After stirring overnight under an atmosphere of dry N2 at ambient temperature, the reaction mixture was concentrated under vacuum and the residue was chromatographed on flash silica gel eluting with a gradient of DCM to MeOH/DCM (2:98) to give 8.55 g of the titled product as a solid.

Workup

  1. concentrationthe reaction mixture was concentrated under vacuum
  2. customthe residue was chromatographed on flash silica gel eluting with a gradient of DCM to MeOH/DCM (2:98)

Sources & evidence

ORD record
ord-3544eff623884eb7860652fd7fda7d01
Source dataset
uspto-grants-2003_11
Patent number
US06645982B2

Reaction notes

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