Sodium Carbonate → 5-Bromo-8-(3,5-dimethoxy-phenyl)-quinoxaline

HRID 43046노트

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HRID 43046 반응식
[CH3:1][O:2][C:3]1[CH:4]=[C:5](B(O)O)[CH:6]=[C:7]([O:9][CH3:10])[CH:8]=1.Br[C:15]1[CH:24]=[CH:23][C:22]([Br:25])=[C:21]2[C:16]=1[N:17]=[CH:18][CH:19]=[N:20]2.C([O-])([O-])=O.[Na+].[Na+]>CCO.C1(C)C=CC=CC=1.CCOC(C)=O.O.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[Br:25][C:22]1[CH:23]=[CH:24][C:15]([C:5]2[CH:4]=[C:3]([O:2][CH3:1])[CH:8]=[C:7]([O:9][CH3:10])[CH:6]=2)=[C:16]2[C:21]=1[N:20]=[CH:19][CH:18]=[N:17]2

참가 물질

9

반응물 3

HCID 10340Sodium CarbonateHCID 4374257(3,5-Dimethoxyphenyl)boronic acidHCID 115147635,8-Dibromoquinoxaline

생성물 1

HCID 592928255-Bromo-8-(3,5-dimethoxy-phenyl)-quinoxaline수율 70.7%

시약·촉매·용매 5

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)촉매HCID 702Ethanol용매HCID 962Water용매HCID 1140Toluene용매HCID 8857Ethyl Acetate용매

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온도
105 °C

실험 절차

A mixture of 3,5-dimethoxyphenylboronic acid (Step 1.8) (3.38 g, 18.6 mmol) in EtOH (15 mL) was added dropwise to a mixture of 5,8-dibromo-quinoxaline (Step 1.5) (10.7 g, 37.1 mmol, 2 equiv), PdCl2(dppf) (530 mg, 0.7 mmol, 0.03 equiv), Na2CO3 (2 M solution in H2O, 37 mL, 74.3 mmol, 4 equiv) in toluene (100 mL) at 105° C., under an argon atmosphere. The reaction mixture was stirred at 105° C. for 2 h, allowed to cool to rt, diluted with EtOAc and H2O, filtered through a pad of celite and extracted with EtOAc. The organic phase was washed with H2O and brine, dried (Na2SO4), filtered and concentrated in vacuo. The crude product was purified by trituration in DCM, followed by silica gel column chromatography (Hex/EtOAc, 4:1) to afford 4.54 g of the title compound as a yellow solid: ES-MS: 345.0 [M+H]+; tR=5.13 min (System 1); Rf=0.17 (Hex/EtOAc, 4:1).

후처리

  1. temperatureto cool to rt
  2. filtrationfiltered through a pad of celite
  3. extractionextracted with EtOAc
  4. washThe organic phase was washed with H2O and brine
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe crude product was purified by trituration in DCM

출처 및 근거

ORD 기록
ord-0b8a36f9e64b48c9b47a8bba000f6514
출처 데이터셋
uspto-grants-2013_09
특허 번호
US08536175B2

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