Potassium Carbonate → Ethyl 3-methylquinoxaline-2-carboxylate

HRID 869674노트

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HRID 869674 반응식
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

참가 물질

7

반응물 4

HCID 11430Potassium CarbonateHCID 312751,4-DioxaneHCID 574072Trimethylboroxine2회HCID 28063031HCID 28063031, 화합물

생성물 1

HCID 589024Ethyl 3-methylquinoxaline-2-carboxylate

시약·촉매·용매 2

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

반응 조건

온도
115 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-4a7b7096c5134fbab93c3c17d90e2645
출처 데이터셋
uspto-grants-2015_03
특허 번호
US08969376B2

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