4-(Trifluoromethoxy)phenylboronic acid → HCID 86718122, compound

HRID 2205135Notes

Reaction equation

HRID 2205135 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.[F:22][C:23]([F:35])([F:34])[O:24][C:25]1[CH:30]=[CH:29][C:28](B(O)O)=[CH:27][CH:26]=1>>[C:16]1([C:3]2[C:2]([C:28]3[CH:29]=[CH:30][C:25]([O:24][C:23]([F:35])([F:34])[F:22])=[CH:26][CH:27]=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 27343864-(Trifluoromethoxy)phenylboronic acidHCID 86667202Methyl 3-bromo-2-phenylquinoxaline-6-carboxylate

Product 1

HCID 86718122HCID 86718122, compoundYield 47.9%

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-(trifluoromethoxy)phenylboronic acid (89.6 mg, 0.43 mmol, 1.50 equiv) as reactants. Purification via silica gel column (dichloromethane/methanol (10:1)) yielded 57 mg (47%) of 2-phenyl-3-(4-(trifluoromethoxy)phenyl)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-12f05b95fe684ed7b9506f04b6349c39
Source dataset
uspto-grants-2016_06
Patent number
US09370522B2

Reaction notes

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