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Potassium Carbonate → 2-Phenyl-3-p-tolyl-pyrido[2,3-b]pyrazine

HRID 406253
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HRID 406253 반응식
Cl[C:2]1[N:3]=[C:4]2[CH:18]=[CH:17][CH:16]=[N:15][C:5]2=[N:6][C:7]=1[C:8]1[CH:13]=[CH:12][C:11]([CH3:14])=[CH:10][CH:9]=1.[C:19]1(B(O)O)[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.C([O-])([O-])=O.[K+].[K+]>O1CCOCC1.O.CCOC(C)=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]>[C:19]1([C:2]2[N:3]=[C:4]3[CH:18]=[CH:17][CH:16]=[N:15][C:5]3=[N:6][C:7]=2[C:8]2[CH:13]=[CH:12][C:11]([CH3:14])=[CH:10][CH:9]=2)[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

8

반응물 3

HCID 11430Potassium CarbonateHCID 66827Phenylboronic AcidHCID 866818592-Chloro-3-p-tolyl-pyrido[2,3-b]pyrazine

생성물 1

HCID 666655042-Phenyl-3-p-tolyl-pyrido[2,3-b]pyrazine

시약·촉매·용매 4

HCID 44119782Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)촉매2회
HCID 962
Water
용매
HCID 8857Ethyl Acetate용매
HCID 312751,4-Dioxane용매

실험 절차

A mixture of 2-chloro-3-p-tolyl-pyrido[2,3-b]pyrazine (800 mg, 3.13 mmol), phenylboronic acid (572 mg, 4.69 mmol) and K2CO3 (1297 mg, 9.39 mmol) in dioxane (10 ml) was degassed by bubbling nitrogen through (×3). PdCl2(dppf) (229 mg, 0.313 mmol) was added and the reaction mixture was degassed by bubbling nitrogen through (×3). The resulting mixture was heated using microwave radiation at 150° C. for 2 hours. PdCl2(dppf) (229 mg, 0.313 mmol) was added and the mixture was heated using microwave radiation at 150° C. for 2 hours. After cooling to RT, the mixture was diluted with water and EtOAc, and filtered through Celite® (filter material). The phases were separated and the aqueous extracted with EtOAc The combined organic extracts were washed with brine, dried over MgSO4 and concentrated in vacuo. The crude product was purified by chromatography on silica eluting with 2-5% THF/DCM to give a contaminated gum. The material was re-purified by chromatography on silica eluting with 0-60% EtOAc/iso-hexane to afford the title compound;

후처리

  1. customwas degassed
  2. customby bubbling nitrogen through (×3)
  3. customthe reaction mixture was degassed
  4. customby bubbling nitrogen through (×3)
  5. temperatureThe resulting mixture was heated
  6. customat 150° C.
  7. customfor 2 hours
  8. temperaturethe mixture was heated
  9. customat 150° C.
  10. customfor 2 hours
  11. filtrationfiltered through Celite® (filter material)
  12. customThe phases were separated
  13. extractionthe aqueous extracted with EtOAc The combined organic extracts
  14. washwere washed with brine
  15. dry with materialdried over MgSO4
  16. concentrationconcentrated in vacuo
  17. customThe crude product was purified by chromatography on silica eluting with 2-5% THF/DCM
  18. customto give a contaminated gum
  19. customThe material was re-purified by chromatography on silica eluting with 0-60% EtOAc/iso-hexane

출처 및 근거

ORD 기록
ord-b636978f001744249c49db3ff72b6bed
출처 데이터셋
uspto-grants-2014_06
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08754085B2

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