O-Xylene → HCID 22319210, compound

HRID 229674Notes

Reaction equation

HRID 229674 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]1[C:10](=[O:34])[N:11]([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[CH:12]=[C:13]([Sn](CCCC)(CCCC)CCCC)[CH:14]=1)#[N:2].[C:35]([O:38][C:39]1[CH:40]=[CH:41][C:42](Cl)=[N:43][CH:44]=1)(=[O:37])[CH3:36].C1(C)C(C)=CC=CC=1>C(OCC)(=O)C.CCCCCC>[C:35]([O:38][C:39]1[CH:40]=[CH:41][C:42]([C:13]2[CH:14]=[C:9]([C:4]3[CH:5]=[CH:6][CH:7]=[CH:8][C:3]=3[C:1]#[N:2])[C:10](=[O:34])[N:11]([C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)[CH:12]=2)=[N:43][CH:44]=1)(=[O:37])[CH3:36]

Participants

5

Reactant 3

HCID 7237O-XyleneHCID 8199305-Acetyloxy-2-chloropyridineHCID 22318968HCID 22318968, compound

Product 1

HCID 22319210HCID 22319210, compoundYield 38.4%

Reagents, catalysts & solvents 1

HCID 21226206Ethyl acetate hexaneSolvent

Conditions

Temperature
120 °C

Procedure

3.42 g of 3-(2-cyanophenyl)-1-phenyl-5-(tri-n-butyl stannyl)-1,2-dihydropyridin-2-one, 1.57 g of 5-acetoxy-2-chloropyridine and 352 mg of tetrakistriphenylphosphine palladium were added to 40 ml of xylene, and the mixture was stirred at 120° C. in a nitrogen atmosphere for 8.5 hours. The reaction mixture was refined by silica gel chromatography (ethyl acetate/hexane-based solvent), to obtain 953 mg of the subject compound.

Sources & evidence

ORD record
ord-ca518133d9e8477f8525bcc3884a338c
Source dataset
uspto-grants-2009_07
Patent number
US07563811B2

Reaction notes

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