3,4-Dimethoxyphenylboronic acid → HCID 86718107, compound

HRID 2205106Notes

Reaction equation

HRID 2205106 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:25]=[C:26](B(O)O)[CH:27]=[CH:28][C:29]=1[O:30][CH3:31]>>[CH3:22][O:23][C:24]1[CH:25]=[C:26]([C:2]2[C:3]([C:16]3[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=3)=[N:4][C:5]3[C:10]([N:11]=2)=[CH:9][C:8]([C:12]([OH:14])=[O:13])=[CH:7][CH:6]=3)[CH:27]=[CH:28][C:29]=1[O:30][CH3:31]

Participants

3

Reactant 2

HCID 27347023,4-Dimethoxyphenylboronic acidHCID 86667202Methyl 3-bromo-2-phenylquinoxaline-6-carboxylate

Product 1

HCID 86718107HCID 86718107, compoundYield 44.6%

Procedure

The ester product was obtained via a Suzuki coupling reaction using the method previously shown in Example 13, Step 6, with methyl 3-bromo-2-phenylquinoxaline-6-carboxylate (100 mg, 0.29 mmol, 1.00 equiv) and 3,4-dimethoxyphenylboronic acid (80 mg, 0.44 mmol, 1.50 equiv) as reactants. Purification by Prep-TLC (silica gel) yielded 50 mg (44%) of 3-(3,4-dimethoxyphenyl)-2-phenylquinoxaline-6-carboxylic acid as a yellow solid.

Workup

  1. customPurification by Prep-TLC (silica gel)

Sources & evidence

ORD record
ord-b69732a470454dd4acbb5d0d7f630e3b
Source dataset
uspto-grants-2016_06
Patent number
US09370522B2

Reaction notes

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