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Potassium Carbonate → 2-Chloro-3-phenylpyrido[2,3-b]pyrazine

HRID 406250
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HRID 406250 반응식
[Cl:1][C:2]1[N:7]=[C:6]2[CH:8]=[CH:9][CH:10]=[N:11][C:5]2=[N:4][C:3]=1Cl.[C:13]1(B(O)O)[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C(=O)([O-])[O-].[K+].[K+]>O1CCOCC1.O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[Cl:1][C:2]1[N:7]=[C:6]2[CH:8]=[CH:9][CH:10]=[N:11][C:5]2=[N:4][C:3]=1[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

7

반응물 3

HCID 11430Potassium CarbonateHCID 66827Phenylboronic AcidHCID 117888682,3-Dichloropyrido[2,3-b]pyrazine

생성물 1

HCID 866818582-Chloro-3-phenylpyrido[2,3-b]pyrazine

시약·촉매·용매 3

HCID 178418397HCID 178418397, 화합물촉매HCID 962Water
용매
2회
HCID 312751,4-Dioxane용매

실험 절차

2,3-Dichloropyrido[2,3-b]pyrazine (step 2) (500 mg, 2.5 mmol) in dry dioxane (10 ml), under nitrogen was treated with phenylboronic acid (305 mg, 2.5 mmol), potassium carbonate (691 mg, 5 mmol) in water (0.5 ml) and tetrakis(triphenylphosphine)palladium(0) (144 mg, 0.125 mmol). The resulting mixture was heated using microwave radiation at 100° C. for 1 hour. After cooling to RT, the mixture was diluted with water (100 ml) and extracted with DCM (×3). The combined organic extracts were washed with brine, dried over MgSO4 and filtered. The solvent was removed in vacuo and the crude product was purified by chromatography on silica eluting with 0-30% EtOAc/iso-hexane to afford the title compound as a solid;

후처리

  1. temperatureThe resulting mixture was heated
  2. customat 100° C.
  3. customfor 1 hour
  4. extractionextracted with DCM (×3)
  5. washThe combined organic extracts were washed with brine
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. customThe solvent was removed in vacuo
  9. customthe crude product was purified by chromatography on silica eluting with 0-30% EtOAc/iso-hexane

출처 및 근거

ORD 기록
ord-388b05f7fc084cfcaef4f7afcf216013
출처 데이터셋
uspto-grants-2014_06
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08754085B2

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