3-Cyanophenylboronic acid → 2,2'-(6-Oxo-1-(1-phenylethyl)-1,6-dihydropyridazine-4,5-diyl)dibenzonitrile

HRID 880376Notes

Reaction equation

HRID 880376 reaction equation
Cl[C:2]1[C:3](=[O:17])[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.[C:18]([C:20]1[CH:21]=[C:22](B(O)O)[CH:23]=[CH:24][CH:25]=1)#[N:19]>>[O:17]=[C:3]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:24]2[CH:25]=[C:20]([CH:21]=[CH:22][CH:23]=2)[C:18]#[N:19])=[C:2]1[C:13]1[CH:12]=[C:11]([CH:16]=[CH:15][CH:14]=1)[C:9]#[N:4].[O:17]=[C:3]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:25]2[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=2[C:18]#[N:19])=[C:2]1[C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=1[C:9]#[N:4]

Participants

4

Reactant 2

HCID 27343253-Cyanophenylboronic acidHCID 680139864,5-dichloro-2-(1-phenylethyl)pyridazin-3(2H)-one

Product 2

HCID 573856312,2'-(6-Oxo-1-(1-phenylethyl)-1,6-dihydropyridazine-4,5-diyl)dibenzonitrileYield 7.4%HCID 573858843,3'-(6-Oxo-1-(1-phenylethyl)-1,6-dihydropyridazine-4,5-diyl) dibenzonitrile

Procedure

Compound 5 is prepared from intermediate 1a and 3-cyanophenylboronic acid under the conditions described for example 4. The minor product formed (solid) corresponds to compound 4 (yield:7.4%).

Sources & evidence

ORD record
ord-a72171a545f64f79a8acb4dcdd0adc41
Source dataset
uspto-grants-2015_03
Patent number
US08993569B2

Reaction notes

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