Potassium Carbonate → HCID 57856035, compound

HRID 1715202Notes

Reaction equation

[C:1]([O:10][CH2:11][CH3:12])(=[O:9])/[CH:2]=[CH:3]\[C:4]([O:6][CH2:7][CH3:8])=[O:5].C([O-])(=O)/C=C/C([O-])=O.Br[C:22]1[CH:23]=[C:24]2[C:29](=[CH:30][CH:31]=1)[N:28]=[CH:27][CH:26]=[N:25]2.C1(C)C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH2:11]([O:10][C:1](=[O:9])[C:2]([C:22]1[CH:23]=[C:24]2[C:29](=[CH:30][CH:31]=1)[N:28]=[CH:27][CH:26]=[N:25]2)=[CH:3][C:4]([O:6][CH2:7][CH3:8])=[O:5])[CH3:12]

Participants

Conditions

Temperature: 100 °C

Procedure

The title compound can be prepared through a palladium mediated coupling reaction, using diethyl maleate or fumarate as a common reagent (e.g. Tetrahedron, 2002, 58, 6545). For example, a mixture of 6-bromoquinoxaline (1 eq.), diethyl maleate (2.3 eq.), palladium acetate (0.05 eq.), tri(o-tolyl)phosphine (0.1 eq.) and potassium carbonate (2 eq.) in DMF may be warmed to 100° C. and stirred for 16 hours. Quenching with water, extraction with diethyl ether and purification of the crude product by flash chromatography should provide the title compound.

Workup

customQuenching with water, extraction with diethyl ether and purification of the crude product by flash chromatography

Sources & evidence

ORD record: ord-8e2be20925aa482db2fc321c7e67b3fd
Source dataset: uspto-grants-2010_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07799815B2

Reaction notes

Loading…