Methyl Acrylate → HCID 86718145, compound

HRID 2205161Notes

Reaction equation

Br[C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[C:7]([C:12]1[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][CH:13]=1)[C:6]([C:20]1[CH:25]=[CH:24][C:23]([O:26][CH3:27])=[CH:22][CH:21]=1)=[N:5]2.[C:28]([O:32][CH3:33])(=[O:31])[CH:29]=[CH2:30].C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>CN(C=O)C.CCN(CC)CC.CC([O-])=O.CC([O-])=O.[Pd+2]>[CH3:19][O:18][C:15]1[CH:14]=[CH:13][C:12]([C:7]2[C:6]([C:20]3[CH:21]=[CH:22][C:23]([O:26][CH3:27])=[CH:24][CH:25]=3)=[N:5][C:4]3[C:9](=[CH:10][CH:11]=[C:2](/[CH:30]=[CH:29]/[C:28]([O:32][CH3:33])=[O:31])[CH:3]=3)[N:8]=2)=[CH:17][CH:16]=1

Participants

Conditions

Temperature: 100 °C

Procedure

A solution of 6-bromo-2,3-bis(4-methoxyphenyl)quinoxaline (100 mg, 0.24 mmol, 1.00 equiv), methyl acrylate (40.8 mg, 0.47 mmol, 2.00 equiv), Pd(OAc)2 (5.3 mg, 0.02 mmol, 0.10 equiv), PPh3 (24.8 mg, 0.09 mmol, 0.40 equiv) in DMF/Et3N (4/2 mL). The resulting solution was stirred overnight at 100° C. under an inert atmosphere. The mixture was concentrated under vacuum and purified via silica gel column (ethyl acetate/petroleum ether (1:30)), yielding 80 mg (79%) of (E)-methyl 3-(2,3-bis(4-methoxyphenyl)quinoxalin-6-yl)acrylate as a yellow solid.

Workup

concentrationThe mixture was concentrated under vacuum
custompurified via silica gel column (ethyl acetate/petroleum ether (1:30))

Sources & evidence

ORD record: ord-4ce32ce317a94ec69158ff5ee914a4b8
Source dataset: uspto-grants-2016_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09370522B2

Reaction notes

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