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

HRID 2276595
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HRID 2276595 반응식
Cl[C:2]1[N:3]=[C:4]2[CH:17]=[CH:16][CH:15]=[N:14][C:5]2=[N:6][C:7]=1[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.B(O)(O)[C:19]1[CH:20]=[CH:21][C:22]([CH3:25])=[CH:23][CH:24]=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>[C:8]1([C:7]2[N:6]=[C:5]3[N:14]=[CH:15][CH:16]=[CH:17][C:4]3=[N:3][C:2]=2[C:19]2[CH:24]=[CH:23][C:22]([CH3:25])=[CH:21][CH:20]=2)[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

7

반응물 3

HCID 11430Potassium CarbonateHCID 79799Tolylboronic acidHCID 866818582-Chloro-3-phenylpyrido[2,3-b]pyrazine

생성물 1

HCID 590904003-Phenyl-2-p-tolylpyrido[2,3-b]pyrazine

시약·촉매·용매 3

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

실험 절차

2-Chloro-3-phenylpyrido[2,3-b]pyrazine (step 3) (175 mg, 0.724 mmol) in dry dioxane (4 ml) under nitrogen was treated with p-tolylboronic acid (108 mg, 0.797 mmol), potassium carbonate (200 mg, 1.448 mmol) in water (0.5 ml) and tetrakis(triphenylphosphine)palladium(0) (41.8 mg, 0.036 mmol). The resulting mixture was heated using microwave radiation at 150° 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 yellow solid;

후처리

  1. temperatureThe resulting mixture was heated
  2. customat 150° 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-928ef7a329204e63976d94e8f84dbada
출처 데이터셋
uspto-grants-2015_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09132127B2

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