Tolylboronic acid → HCID 86718105, compound

HRID 2205104Notes

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.B(O)(O)[C:23]1[CH:24]=[CH:25][C:26]([CH3:29])=[CH:27][CH:28]=1>>[C:16]1([C:3]2[C:2]([C:23]3[CH:28]=[CH:27][C:26]([CH3:29])=[CH:25][CH:24]=3)=[N:11][C:10]3[C:5](=[CH:6][CH:7]=[C:8]([C:12]([O:14][CH3:15])=[O:13])[CH:9]=3)[N:4]=2)[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

Reactant 2

HCID 79799Tolylboronic acid

HCID 77231183Methyl 3-chloro-2-phenylquinoxaline-6-carboxylate

Product 1

HCID 86718105HCID 86718105, compoundYield 76%

Procedure

The ester product was obtained via a Suzuki coupling reaction using the method previously shown in Example 13, Step 6. Methyl 3-chloro-2-phenylquinoxaline-6-carboxylate (100 mg, 0.34 mmol, 1.00 equiv) and p-tolylboronic acid (54 mg, 0.4 mmol, 1.10 equiv) were used as starting materials and chromatography was performed with ethyl acetate/petroleum ether (1:20) as the eluent, affording 90 mg (76%) of methyl 2-phenyl-3-p-tolylquinoxaline-6-carboxylate as a yellow solid.

Sources & evidence

ORD record: ord-a89cf1ab792e4e49baab7ac571374d58
Source dataset: uspto-grants-2016_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09370522B2

Reaction notes

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