4-Benzoylbenzeneboronic acid → 3-(4-Benzoylphenyl)-5-chloroisonicotinonitrile

HRID 81030Notes

Reaction equation

HRID 81030 reaction equation
Cl[C:2]1[CH:9]=[N:8][CH:7]=[C:6]([Cl:10])[C:3]=1[C:4]#[N:5].[C:11]([C:19]1[CH:24]=[CH:23][C:22](B(O)O)=[CH:21][CH:20]=1)(=[O:18])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1>>[C:11]([C:19]1[CH:24]=[CH:23][C:22]([C:2]2[CH:9]=[N:8][CH:7]=[C:6]([Cl:10])[C:3]=2[C:4]#[N:5])=[CH:21][CH:20]=1)(=[O:18])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

3

Reactant 2

HCID 41972354-Benzoylbenzeneboronic acidHCID 111375993,5-Dichloropyridine-4-carbonitrile

Product 1

HCID 669274923-(4-Benzoylphenyl)-5-chloroisonicotinonitrileYield 80%

Procedure

Following conditions described in Step 1 of Example 50, 3,5-dichloroisonicotinonitrile was reacted with 4-benzoylphenylboronic acid to give 3-(4-benzoylphenyl)-5-chloroisonicotinonitrile (˜80% pure). MS (ES+) m/z: 351 (M+H); LC retention time: 3.980 min (analytical HPLC Method A). Step 2:

Sources & evidence

ORD record
ord-4ec763ac4b0744248fdb65cf47173274
Source dataset
uspto-grants-2014_09
Patent number
US08846673B2

Reaction notes

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