3-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenol → 2-Amino-5-(3-hydroxy-phenyl)-N-pyridin-4-yl-nicotinamide

HRID 919249Notes

Reaction equation

HRID 919249 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].[OH:18][C:19]1[CH:20]=[C:21](B2OC(C)(C)C(C)(C)O2)[CH:22]=[CH:23][CH:24]=1>>[NH2:1][C:2]1[N:16]=[CH:15][C:14]([C:23]2[CH:22]=[CH:21][CH:20]=[C:19]([OH:18])[CH:24]=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

3

Reactant 2

HCID 27346233-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenolHCID 621554162-amino-5-bromo-N-(pyridin-4-yl)nicotinamide

Product 1

HCID 710627782-Amino-5-(3-hydroxy-phenyl)-N-pyridin-4-yl-nicotinamide

Procedure

Reaction of 2-amino-5-bromo-N-pyridin-4-yl-nicotinamide with 3-hydroxyphenyl-boronic acid pinacol ester gives “A70”; method 1: HPLC/MS: 1.12 min, [M+H]=307.

Workup

  1. customgives “A70”
  2. custom1.12 min, [M+H]=307

Sources & evidence

ORD record
ord-01c6068832184c29ad85c5176da1f477
Source dataset
uspto-grants-2016_03
Patent number
US09273029B2

Reaction notes

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