1-Naphthaleneboronic acid → HCID 86718109, compound

HRID 2205108Notes

Reaction equation

HRID 2205108 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]1(B(O)O)[C:31]2[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=2)[CH:25]=[CH:24][CH:23]=1>>[C:30]1([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)[C:31]2[C:26](=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH:27]=[CH:28][CH:29]=1

Participants

3

Reactant 2

HCID 2545321-Naphthaleneboronic acidHCID 77231183Methyl 3-chloro-2-phenylquinoxaline-6-carboxylate

Product 1

HCID 86718109HCID 86718109, compoundYield 69%

Procedure

The ester product was obtained via a Suzuki coupling reaction using the method previously shown in Example 13, Step 6, using methyl 3-chloro-2-phenylquinoxaline-6-carboxylate (100 mg, 0.34 mmol, 1.00 equiv) and naphthalen-1-yl boronic acid (63 mg, 0.37 mmol, 1.10 equiv) as reactants. Purification via silica gel column (ethyl acetate/petroleum ether (1:20)) afforded 90 mg (69%) of methyl 3-(naphthalen-1-yl)-2-phenylquinoxaline-6-carboxylate as a yellow powder.

Workup

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

Sources & evidence

ORD record
ord-2afd677b3d6046af9df0e9397c8ec52a
Source dataset
uspto-grants-2016_06
Patent number
US09370522B2

Reaction notes

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