Boronic Acid → 8-(3-Methyl-4-morpholin-4-ylmethyl-phenyl)-2-(3,4,5-trimethoxy-phenyl)-quinoxaline

HRID 216730Notes

Reaction equation

HRID 216730 reaction equation
BrC1C=CC=[C:6]2[C:11]=1[N:10]=[C:9]([C:12]1[CH:17]=[CH:16][C:15](OC)=[C:14](OC)[CH:13]=1)C=N2.C[O:23][C:24]1C(OC)=CC(B(O)O)=C[CH:25]=1.[CH3:35]OC1C=C(B(O)O)C=C(OC)C=1OC.Br[C:51]1[CH:52]=[CH:53][CH:54]=[C:55]2[C:60]=1[N:59]=[C:58]([C:61]1[CH:66]=[C:65]([O:67][CH3:68])[C:64]([O:69][CH3:70])=[C:63]([O:71][CH3:72])[CH:62]=1)[CH:57]=[N:56]2.B(O)O>>[CH3:35][C:17]1[CH:16]=[C:15]([C:51]2[CH:52]=[CH:53][CH:54]=[C:55]3[C:60]=2[N:59]=[C:58]([C:61]2[CH:66]=[C:65]([O:67][CH3:68])[C:64]([O:69][CH3:70])=[C:63]([O:71][CH3:72])[CH:62]=2)[CH:57]=[N:56]3)[CH:14]=[CH:13][C:12]=1[CH2:9][N:10]1[CH2:11][CH2:6][O:23][CH2:24][CH2:25]1

Participants

6

Reactant 5

HCID 61668Boronic AcidHCID 27343903,4,5-Trimethoxybenzeneboronic acidHCID 27347023,4-Dimethoxyphenylboronic acidHCID 59392828HCID 59392828, compoundHCID 675397498-Bromo-2-(3,4-dimethoxy-phenyl)-quinoxaline

Product 1

HCID 251238088-(3-Methyl-4-morpholin-4-ylmethyl-phenyl)-2-(3,4,5-trimethoxy-phenyl)-quinoxaline

Procedure

Using the same synthetic methods as described in Example 1, but utilizing 8-Bromo-2-(3,4-dimethoxy-phenyl)-quinoxaline [prepared analogously to step 1.5 but utilizing 4,5-dimethoxyphenylboronic acid in lieu of 3,4,5-trimethoxyphenylboronic acid] in lieu of 8-Bromo-2-(3,4,5-trimethoxy-phenyl)-quinoxaline and the appropriate boronic acid or ester derivative leads to the following Examples

Workup

  1. customprepared analogously to step 1.5

Sources & evidence

ORD record
ord-82f47db11059420da4b0ac6158ba855e
Source dataset
uspto-grants-2012_06
Patent number
US08193189B2

Reaction notes

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