4,4,5,5-Tetramethyl-2-(4-nitrophenyl)-1,3,2-dioxaborolane → HCID 86718125, compound

HRID 2205139Notes

Reaction equation

HRID 2205139 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.CC1(C)C(C)(C)OB([C:30]2[CH:35]=[CH:34][C:33]([N+:36]([O-:38])=[O:37])=[CH:32][CH:31]=2)O1>>[N+:36]([C:33]1[CH:34]=[CH:35][C:30]([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:31][CH:32]=1)([O-:38])=[O:37]

Participants

3

Reactant 2

HCID 27735554,4,5,5-Tetramethyl-2-(4-nitrophenyl)-1,3,2-dioxaborolaneHCID 86667202Methyl 3-bromo-2-phenylquinoxaline-6-carboxylate

Product 1

HCID 86718125HCID 86718125, 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 4,4,5,5-tetramethyl-2-(4-nitrophenyl)-1,3,2-dioxaborolane (144.4 mg, 0.58 mmol, 2.00 equiv) as reactants. Purification via silica gel column (dichloromethane/methanol (10:1)) afforded 27 mg (24%) of 3-(4-nitrophenyl)-2-phenylquinoxaline-6-carboxylic acid as a yellow 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-af6f051850d24ddfae9565e7b58dae71
Source dataset
uspto-grants-2016_06
Patent number
US09370522B2

Reaction notes

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