4-Cyanophenylboronic acid → HCID 86718112, compound

HRID 2205113Notes

Reaction equation

HRID 2205113 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][CH3:15])=[O:13])=[CH:7][CH:6]=2.[C:22]([C:24]1[CH:29]=[CH:28][C:27](B(O)O)=[CH:26][CH:25]=1)#[N:23]>>[C:22]([C:24]1[CH:29]=[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]([O:14][CH3:15])=[O:13])=[CH:7][CH:6]=3)=[CH:26][CH:25]=1)#[N:23]

Participants

3

Reactant 2

HCID 27343264-Cyanophenylboronic acidHCID 77231183Methyl 3-chloro-2-phenylquinoxaline-6-carboxylate

Product 1

HCID 86718112HCID 86718112, compoundYield 74.6%

Procedure

The ester product was obtained via a Suzuki coupling reaction using the method previously shown in Example 13, Step 6, with methyl 3-chloro-2-phenylquinoxaline-6-carboxylate (100 mg, 0.33 mmol, 1.00 equiv) and 4-cyanophenylboronic acid (74 mg, 0.50 mmol, 1.50 equiv) as reactants. Purification via silica gel column (ethyl acetate/petroleum ether (1:20 to 1:10)) afforded 90 mg (73%) of methyl 3-(4-cyanophenyl)-2-phenylquinoxaline-6-carboxylate as a yellow solid.

Workup

  1. customPurification via silica gel column (ethyl acetate/petroleum ether (1:20 to 1:10))

Sources & evidence

ORD record
ord-75784192454b42d8ad8b0631ab08539e
Source dataset
uspto-grants-2016_06
Patent number
US09370522B2

Reaction notes

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