1,1'-Biphenyl-4-yl-boronic acid → HCID 86718130, compound

HRID 2205145Notes

Reaction equation

HRID 2205145 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.[C:22]1([C:28]2[CH:33]=[CH:32][C:31](B(O)O)=[CH:30][CH:29]=2)[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>>[C:16]1([C:3]2[C:2]([C:31]3[CH:32]=[CH:33][C:28]([C:22]4[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=4)=[CH:29][CH:30]=3)=[N:11][C:10]3[C:5](=[CH:6][CH:7]=[C:8]([C:12]([OH:14])=[O:13])[CH:9]=3)[N:4]=2)[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1

Participants

3

Reactant 2

HCID 1512531,1'-Biphenyl-4-yl-boronic acidHCID 86667202Methyl 3-bromo-2-phenylquinoxaline-6-carboxylate

Product 1

HCID 86718130HCID 86718130, compoundYield 51.4%

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-phenyl-phenylboronic acid (100 mg, 0.51 mmol, 1.50 equiv) as reactants. Purification via silica gel column (dichloromethane/methanol (15:1)) yielded 60 mg (51%) of 2-phenyl-3-(4-phenyl-phenyl)quinoxaline-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 (15:1))

Sources & evidence

ORD record
ord-3ef5790215724732ad58194d494dcf2e
Source dataset
uspto-grants-2016_06
Patent number
US09370522B2

Reaction notes

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