Potassium Carbonate → Ethyl 3-methylquinoxaline-2-carboxylate

HRID 869674ノート

反応式

HRID 869674 の反応式
Cl[C:2]1[C:3]([C:12]([O-:14])=[O:13])=[N:4][C:5]2[C:10]([N:11]=1)=[CH:9][CH:8]=[CH:7][CH:6]=2.CB1OB(C)OB(C)O1.[C:24](=O)([O-])[O-].[K+].[K+].O1CCO[CH2:32][CH2:31]1>C(OCC)(=O)C.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]>[CH3:24][C:2]1[C:3]([C:12]([O:14][CH2:31][CH3:32])=[O:13])=[N:4][C:5]2[C:10]([N:11]=1)=[CH:9][CH:8]=[CH:7][CH:6]=2

参加物

7

反応物 4

HCID 11430Potassium CarbonateHCID 312751,4-DioxaneHCID 574072Trimethylboroxine2 回HCID 28063031HCID 28063031、化合物

生成物 1

HCID 589024Ethyl 3-methylquinoxaline-2-carboxylate

試薬・触媒・溶媒 2

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

反応条件

温度
115 °C

実験手順

A suspension of 3-chloroquinoxaline-2-carboxylate (86.0 g, 363 mmol), trimethylboroxine (22.8 g, 0.182 mmol), [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II) (8.90 g, 11.0 mmol), and potassium carbonate (100 g, 727 mmol) in 1,4-dioxane (726 mL) was heated at 115° C. for 4 h. And then trimethylboroxine (22.8 g, 0.182 mmol) was added again and heated at same temperature for 2 h. After being cooled to ambient temperature, the reaction mixture was diluted with ethyl acetate (700 mL) and filtrated through celite with ethyl acetate (1000 mL). The filtrate was combined and concentrated in vacuo. The residue was purified by silica gel column chromatography (silica gel 900 g, hexane:ethyl acetate=9:1 to 17:3) followed by recrystallization from cold hexane to give ethyl 3-methylquinoxaline-2-carboxylate. MS (APCI): m/z 217 (M+H).

後処理

  1. temperatureheated at same temperature for 2 h
  2. temperatureAfter being cooled to ambient temperature
  3. filtrationfiltrated through celite with ethyl acetate (1000 mL)
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by silica gel column chromatography (silica gel 900 g, hexane:ethyl acetate=9:1 to 17:3)
  6. customfollowed by recrystallization from cold hexane

出典と根拠

ORDレコード
ord-4a7b7096c5134fbab93c3c17d90e2645
出典データセット
uspto-grants-2015_03
特許番号
US08969376B2

反応ノート

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