2-Methoxyphenylboronic acid → HCID 57378390, compound

HRID 1802255Notes

Reaction equation

HRID 1802255 reaction equation
Br[C:2]1[N:27]=[C:5]2[CH:6]=[C:7]([NH:10][C:11]([C:13]3[N:17]([CH3:18])[N:16]=[CH:15][C:14]=3[C:19]([N:21]3[CH2:26][CH2:25][O:24][CH2:23][CH2:22]3)=[O:20])=[O:12])[CH:8]=[CH:9][N:4]2[N:3]=1.[CH3:28][O:29][C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=1B(O)O>>[CH3:28][O:29][C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=1[C:2]1[N:27]=[C:5]2[CH:6]=[C:7]([NH:10][C:11]([C:13]3[N:17]([CH3:18])[N:16]=[CH:15][C:14]=3[C:19]([N:21]3[CH2:26][CH2:25][O:24][CH2:23][CH2:22]3)=[O:20])=[O:12])[CH:8]=[CH:9][N:4]2[N:3]=1

Participants

3

Reactant 2

HCID 27339582-Methoxyphenylboronic acidHCID 67775604HCID 67775604, compound

Product 1

HCID 57378390HCID 57378390, compoundYield 51.3%

Procedure

The product was prepared in the same manner as described in example 66 using N-(2-bromo-[1,2,4]triazolo[1,5-a]pyridin-7-yl)-1-methyl-4-(morpholine-4-carbonyl)-1H-pyrazole-5-carboxamide (200 mg, 461 μmol) and 2-methoxyphenylboronic acid (140 mg, 921 μmol) as starting materials. The crude material was applied on silicagel and purified by flash chromatography over a 20 g silicagel column using ethyl acetate/methanol 10% as eluent affording 2-methyl-4-(morpholine-4-carbonyl)-2H-pyrazole-3-carboxylic acid [2-(2-methoxy-phenyl)-[1,2,4]triazolo[1,5-a]pyridin-7-yl]-amide (109 mg, 51.3%) as a light brown foam. MS: m/z=462.5 (M+H+).

Workup

  1. customThe product was prepared in the same manner
  2. custompurified by flash chromatography over a 20 g silicagel column

Sources & evidence

ORD record
ord-daac39aab6aa409b8bb62015cddc67be
Source dataset
uspto-grants-2013_01
Patent number
US08349824B2

Reaction notes

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