3-Fluorophenylboronic acid → HCID 86718124, compound

HRID 2205137Notes

Reaction equation

HRID 2205137 reaction equation
Cl[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]1[CH:24]=[C:25](B(O)O)[CH:26]=[CH:27][CH:28]=1>>[F:22][C:23]1[CH:28]=[C:27]([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:26]=[CH:25][CH:24]=1

Participants

3

Reactant 2

HCID 27339863-Fluorophenylboronic acidHCID 77231183Methyl 3-chloro-2-phenylquinoxaline-6-carboxylate

Product 1

HCID 86718124HCID 86718124, compoundYield 58.1%

Procedure

The product was obtained via a Suzuki coupling reaction using the method previously shown in Example 20, Step 3, using methyl 3-chloro-2-phenylquinoxaline-6-carboxylate (90 mg, 0.30 mmol, 1.00 equiv) and 3-fluorophenylboronic acid (63.4 mg, 0.45 mmol, 1.50 equiv) as reactants. Purification via silica gel column (dichloromethane/methanol (10:1)) yielded 60 mg (55%) of 3-(3-fluorophenyl)-2-phenylquinoxaline-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 (10:1))

Sources & evidence

ORD record
ord-ca45ce6a751f43d1b409f2972c891746
Source dataset
uspto-grants-2016_06
Patent number
US09370522B2

Reaction notes

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