3-Carboxyphenylboronic acid → HCID 86718136, compound

HRID 2205150Notes

Reaction equation

HRID 2205150 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][CH3:15])=[O:13])=[CH:7][CH:6]=2.[C:22]([C:25]1[CH:26]=[C:27](B(O)O)[CH:28]=[CH:29][CH:30]=1)([OH:24])=[O:23]>>[C:22]([C:25]1[CH:30]=[C:29]([C:2]2[C:3]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)=[N:4][C:5]3[C:10]([N:11]=2)=[CH:9][C:8]([C:12]([O:14][CH3:15])=[O:13])=[CH:7][CH:6]=3)[CH:28]=[CH:27][CH:26]=1)([OH:24])=[O:23]

Participants

3

Reactant 2

HCID 27339573-Carboxyphenylboronic acidHCID 86667202Methyl 3-bromo-2-phenylquinoxaline-6-carboxylate

Product 1

HCID 86718136HCID 86718136, compoundYield 83.8%

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 (150 mg, 0.44 mmol, 1.00 equiv) and 3-carboxyphenylboronic acid (145.6 mg, 0.88 mmol, 2.00 equiv) as reactants. Purification via silica gel column (DCM/MeOH (20:1)) yielded 141.8 mg (78%) of methyl 3-(3-carboxyphenyl)-2-phenylquinoxaline-6-carboxylate as a white solid.

Workup

  1. customThe product was obtained via a Suzuki coupling reaction
  2. customPurification via silica gel column (DCM/MeOH (20:1))

Sources & evidence

ORD record
ord-3843a0f096e045d9853a92a354a8b7b4
Source dataset
uspto-grants-2016_06
Patent number
US09370522B2

Reaction notes

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