Ethyl 2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate → 2-[6-Amino-5-(pyridin-4-ylcarbamoyl)-pyridin-3-yl]-benzoic acid ethyl ester

HRID 919250Notes

Reaction equation

HRID 919250 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].[CH2:18]([O:20][C:21](=[O:37])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=1B1OC(C)(C)C(C)(C)O1)[CH3:19]>>[CH2:18]([O:20][C:21](=[O:37])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=1[C:14]1[CH:15]=[N:16][C:2]([NH2:1])=[C:3]([C:4](=[O:5])[NH:6][C:7]2[CH:12]=[CH:11][N:10]=[CH:9][CH:8]=2)[CH:13]=1)[CH3:19]

Participants

3

Reactant 2

HCID 2773962Ethyl 2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoateHCID 621554162-amino-5-bromo-N-(pyridin-4-yl)nicotinamide

Product 1

HCID 710607712-[6-Amino-5-(pyridin-4-ylcarbamoyl)-pyridin-3-yl]-benzoic acid ethyl ester

Procedure

Reaction of 2-amino-5-bromo-N-pyridin-4-yl-nicotinamide with ethyl-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate gives “A70”; method 1: HPLC/MS: 1.37 min, [M+H]=363;

Workup

  1. customgives “A70”
  2. custom1.37 min, [M+H]=363

Sources & evidence

ORD record
ord-a6b54524825443aaa4858ab22f605ddb
Source dataset
uspto-grants-2016_03
Patent number
US09273029B2

Reaction notes

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