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

HRID 43216ノート

反応式

HRID 43216 の反応式
[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

参加物

9

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 5

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)触媒HCID 702Ethanol溶媒HCID 962Water溶媒HCID 1140Toluene溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
105 °C

実験手順

A mixture of 3,5-dimethoxyphenylboronic acid (3.38 g, 18.6 mmol) in EtOH (15 mL) was added dropwise to a mixture of 5,8-dibromo-quinoxaline (Step 179.5) (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 [M+H]+; tR=5.13 min (System 1); Rf=0.17 (Hex/EtOAc, 4:1).

後処理

  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

出典と根拠

ORDレコード
ord-fd9dcd28be8e4f8e96de3408ed8648a5
出典データセット
uspto-grants-2013_09
特許番号
US08536175B2

反応ノート

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