(4-Aminophenyl)boronic acid hydrochloride → 2-Amino-5-(4-amino-phenyl)-N-pyridin-4-yl-nicotinamide

Reaction equation

[NH2:1][C:2]1[N:16]=[CH:15][C:14](Br)=[CH:13][C:3]=1[C:4]([NH:6][C:7]1[CH:12]=[CH:11][N:10]=[CH:9][CH:8]=1)=[O:5].Cl.[NH2:19][C:20]1[CH:25]=[CH:24][C:23](B(O)O)=[CH:22][CH:21]=1>>[NH2:1][C:2]1[N:16]=[CH:15][C:14]([C:23]2[CH:24]=[CH:25][C:20]([NH2:19])=[CH:21][CH:22]=2)=[CH:13][C:3]=1[C:4]([NH:6][C:7]1[CH:12]=[CH:11][N:10]=[CH:9][CH:8]=1)=[O:5]

Participants

Reactant 2

HCID 2734614(4-Aminophenyl)boronic acid hydrochloride

HCID 621554162-amino-5-bromo-N-(pyridin-4-yl)nicotinamide

Product 1

HCID 867191552-Amino-5-(4-amino-phenyl)-N-pyridin-4-yl-nicotinamide

Procedure

Reaction of 2-amino-5-bromo-N-pyridin-4-yl-nicotinamide with 4-aminophenyl-boronic acid hydrochloride gives “A65”; method 2: HPLC/MS: 1.53 min, [M+H]=306;

Workup

customgives “A65”
custom1.53 min, [M+H]=306

Sources & evidence

ORD record: ord-c190f9a874af426e90e4ae6dc49f85d4
Source dataset: uspto-grants-2016_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09273029B2

Reaction notes

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