4-Chlorophenylboronic acid → HCID 86718117, compound

HRID 2205129Notes

Reaction equation

HRID 2205129 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.[Cl:22][C:23]1[CH:28]=[CH:27][C:26](B(O)O)=[CH:25][CH:24]=1>>[Cl:22][C:23]1[CH:28]=[CH:27][C:26]([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]([OH:14])=[O:13])=[CH:7][CH:6]=3)=[CH:25][CH:24]=1

Participants

3

Reactant 2

HCID 742994-Chlorophenylboronic acidHCID 86667202Methyl 3-bromo-2-phenylquinoxaline-6-carboxylate

Product 1

HCID 86718117HCID 86718117, compoundYield 41.1%

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 4-chlorophenylboronic acid (87 mg, 0.56 mmol, 1.50 equiv) as reactants. Purification via silica gel column (dichloromethane/methanol (5:1)) afforded 43 mg (37%) of 3-(4-chlorophenyl)-2-phenylquinoxaline-6-carboxylic acid as a light yellow solid.

Workup

  1. customThe product was obtained via a Suzuki coupling reaction
  2. customPurification via silica gel column (dichloromethane/methanol (5:1))

Sources & evidence

ORD record
ord-0b5bbb5f2c154f1898752554493aeb30
Source dataset
uspto-grants-2016_06
Patent number
US09370522B2

Reaction notes

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