2,4-Dimethoxybenzeneboronic acid → HCID 86718128, compound

HRID 2205143Notes

Reaction equation

HRID 2205143 reaction equation
Br[C:2]1[C:3]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[N:4][C:5]2[C:10]([N:11]=1)=[CH:9][C:8]([C:12]([O:14]C)=[O:13])=[CH:7][CH:6]=2.[CH3:22][O:23][C:24]1[CH:29]=[C:28]([O:30][CH3:31])[CH:27]=[CH:26][C:25]=1B(O)O>>[CH3:22][O:23][C:24]1[CH:29]=[C:28]([O:30][CH3:31])[CH:27]=[CH:26][C:25]=1[C:2]1[C:3]([C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=2)=[N:4][C:5]2[C:10]([N:11]=1)=[CH:9][C:8]([C:12]([OH:14])=[O:13])=[CH:7][CH:6]=2

Participants

3

Reactant 2

HCID 27343412,4-Dimethoxybenzeneboronic acidHCID 86667202Methyl 3-bromo-2-phenylquinoxaline-6-carboxylate

Product 1

HCID 86718128HCID 86718128, compoundYield 18.7%

Procedure

The product was obtained via a Suzuki coupling reaction using the method previously shown in Example 20, Step 3, using methyl 3-bromo-2-phenylquinoxaline-6-carboxylate (100 mg, 0.29 mmol, 1.00 equiv) and 2,4-dimethoxyphenylboronic acid (103.7 mg, 0.57 mmol, 1.50 equiv) as reactants. Purification via silica gel column (dichloromethane/methanol (10:1)) afforded 21 mg (18%) of 3-(2,4-dimethoxyphenyl)-2-phenylquinoxaline-6-carboxylic acid as a yellow solid.

Workup

  1. customThe product was obtained via a Suzuki coupling reaction
  2. customPurification via silica gel column (dichloromethane/methanol (10:1))

Sources & evidence

ORD record
ord-967a8a7770684cef82029826a99e4a83
Source dataset
uspto-grants-2016_06
Patent number
US09370522B2

Reaction notes

Loading…