Sodium Carbonate → HCID 59392828, compound

HRID 216729Notes

Reaction equation

HRID 216729 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[N:10]=[C:9](Cl)[CH:8]=[N:7]2.[CH3:13][O:14][C:15]1[CH:16]=[C:17](B(O)O)[CH:18]=[C:19]([O:23][CH3:24])[C:20]=1[O:21][CH3:22].C([O-])([O-])=O.[Na+].[Na+]>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[Br:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[N:10]=[C:9]([C:17]1[CH:18]=[C:19]([O:23][CH3:24])[C:20]([O:21][CH3:22])=[C:15]([O:14][CH3:13])[CH:16]=1)[CH:8]=[N:7]2

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 27343903,4,5-Trimethoxybenzeneboronic acidHCID 593926708-Bromo-2-chloroquinoxaline

Product 1

HCID 59392828HCID 59392828, compound

Reagents, catalysts & solvents 1

HCID 178418397HCID 178418397, compoundCatalyst

Conditions

Temperature
105 °C

Procedure

A microwave tube is charged with 30 mg (0.123 mmol) of 8-Bromo-2-chloro-quinoxaline, 26.4 mg (0.123 mmol) of 3,4,5-trimethoxyphenylboronic acid, 40 mg (0.370 mmol) of Na2CO3 and 4.4 mg (0.0037 mmol) of Pd(PPh3)4. After several cycles of vacuum/purge with argon, 1.5 ml of dry DMF are added. The reaction mixture is then heated tot 105° C. for 15 h. After cooling, the yellow suspension is poured onto de-ionized water and filtered. After drying under H.V. at 50° C., the residue is purified by chromatography (silicagel, hexane:EtOAc=100=>1:1) to afford the title compound as a yellow solid, Rt=1.294 min (Acquity HPLC BEH C18, 2.1×50 mm, 1.7 micron, detection 215 nM, 0.1 min 2% CH3CN in H2O, 2% to 100% CH3CN in H2O in 1.5 min, 0.4 min 100% CH3CN+0.1% TFA, flow rate 1.0 ml/min); MS: 375 (M)+.

Workup

  1. customAfter several cycles of vacuum/purge with argon, 1.5 ml of dry DMF
  2. additionare added
  3. temperatureAfter cooling
  4. additionthe yellow suspension is poured onto de-ionized water
  5. filtrationfiltered
  6. customAfter drying under H.V
  7. customat 50° C., the residue is purified by chromatography (silicagel, hexane:EtOAc=100=>1:1)

Sources & evidence

ORD record
ord-b3e62f2e5c314f89be236689064f7155
Source dataset
uspto-grants-2012_06
Patent number
US08193189B2

Reaction notes

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