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

HRID 406253
ノート
印刷プレビュー

反応式

HRID 406253 の反応式
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
参加物実験手順後処理出典と根拠反応ノート

参加物

8

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 4

HCID 44119782Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)触媒2 回
HCID 962
Water
溶媒
HCID 8857Ethyl Acetate溶媒
HCID 312751,4-Dioxane溶媒

実験手順

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;

後処理

  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

出典と根拠

ORDレコード
ord-b636978f001744249c49db3ff72b6bed
出典データセット
uspto-grants-2014_06
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08754085B2

反応ノート

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