Thiophene-3-boronic acid → HCID 86718127, compound

HRID 2205141Notes

Reaction equation

HRID 2205141 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.[S:22]1[CH:26]=[CH:25][C:24](B(O)O)=[CH:23]1>>[C:16]1([C:3]2[C:2]([C:24]3[CH:25]=[CH:26][S:22][CH:23]=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:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

3

Reactant 2

HCID 581760Thiophene-3-boronic acidHCID 86667202Methyl 3-bromo-2-phenylquinoxaline-6-carboxylate

Product 1

HCID 86718127HCID 86718127, compoundYield 41.5%

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 thiophen-3-ylboronic acid (55.7 mg, 0.44 mmol, 1.50 equiv) as reactants. Purification via silica gel column (dichloromethane/methanol (10:1)) afforded 40 mg (39%) of 2-phenyl-3-(thiophen-3-yl)quinoxaline-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-8572ecd8d7dd4ecb924bed0d9fee8a42
Source dataset
uspto-grants-2016_06
Patent number
US09370522B2

Reaction notes

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