Furan-3-boronic acid → HCID 86718126, compound

HRID 2205140Notes

Reaction equation

HRID 2205140 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.[O:22]1[CH:26]=[CH:25][C:24](B(O)O)=[CH:23]1>>[O:22]1[CH:26]=[CH:25][C:24]([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:23]1

Participants

3

Reactant 2

HCID 2734358Furan-3-boronic acidHCID 86667202Methyl 3-bromo-2-phenylquinoxaline-6-carboxylate

Product 1

HCID 86718126HCID 86718126, compoundYield 25.1%

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 furan-3-yl boronic acid (48.8 mg, 0.44 mmol, 1.50 equiv) as reactants. Purification via silica gel column (dichloromethane/methanol (10:1)) yielded 23 mg (24%) of 3-(furan-3-yl)-2-phenylquinoxaline-6-carboxylic acid as a white 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-954dcd1eee954dd9a67a0163e64a7645
Source dataset
uspto-grants-2016_06
Patent number
US09370522B2

Reaction notes

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