Sodium Carbonate → 2,2'-(6-Oxo-1-(1-phenylethyl)-1,6-dihydropyridazine-4,5-diyl)dibenzonitrile

HRID 880375

Reaction equation

HRID 880375 reaction equation
Cl[C:2]1[C:3](=O)[N:4]([CH:9]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH3:10])[N:5]=[CH:6][C:7]=1Cl.CC1(C)C(C)(C)OB([C:26]2[CH:33]=[CH:32][CH:31]=[CH:30][C:27]=2[C:28]#[N:29])O1.[C:35]([O-:38])([O-])=O.[Na+].[Na+].O.[C:42](#[N:44])[CH3:43]>Cl[Pd]Cl>[O:38]=[C:35]1[N:4]([CH:9]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH3:10])[N:5]=[CH:6][C:7]([C:30]2[CH:31]=[CH:32][CH:33]=[CH:26][C:27]=2[C:28]#[N:29])=[C:2]1[C:3]1[CH:6]=[CH:7][CH:2]=[CH:3][C:43]=1[C:42]#[N:44]

Participants

6

Reactant 4

HCID 10340Sodium CarbonateHCID 35702292-(2-Cyanophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolaneHCID 18373917Acetonitrile--water (1/1)HCID 680139864,5-dichloro-2-(1-phenylethyl)pyridazin-3(2H)-one

Product 1

HCID 573856312,2'-(6-Oxo-1-(1-phenylethyl)-1,6-dihydropyridazine-4,5-diyl)dibenzonitrileYield 3.4%

Reagents, catalysts & solvents 1

HCID 24290Palladium ChlorideCatalyst

Procedure

Compound 4 is prepared from the intermediate 1a and 2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzonitrile according to step 1 of the method of synthesis using PdCl2/2PPh3, Na2CO3 and a mixture of water/acetonitrile: 1/1. The minor product formed corresponds to compound 4 (yield: 3.4%).

Sources & evidence

ORD record
ord-df0cc13c5705491984ec678e116cfc26
Source dataset
uspto-grants-2015_03
Patent number
US08993569B2

Linked notes

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