6-Chloro-1-(6-fluoropyridin-2-yl)-1H-pyrazolo[4,3-c]pyridine → 6-(6-Ethylpyrazin-2-yl)-1-(6-fluoro-2-pyridyl)pyrazolo[4,3-c]pyridine

HRID 57856

반응식

HRID 57856 반응식
Cl[C:2]1[N:7]=[CH:6][C:5]2[CH:8]=[N:9][N:10]([C:11]3[CH:16]=[CH:15][CH:14]=[C:13]([F:17])[N:12]=3)[C:4]=2[CH:3]=1.[CH2:18]([C:20]1[N:25]=[C:24]([Sn](C)(C)C)[CH:23]=[N:22][CH:21]=1)[CH3:19]>CN(C)C(=O)C.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>[CH2:18]([C:20]1[N:25]=[C:24]([C:2]2[N:7]=[CH:6][C:5]3[CH:8]=[N:9][N:10]([C:11]4[CH:16]=[CH:15][CH:14]=[C:13]([F:17])[N:12]=4)[C:4]=3[CH:3]=2)[CH:23]=[N:22][CH:21]=1)[CH3:19]

참가 물질

5

반응물 2

HCID 862802436-Chloro-1-(6-fluoropyridin-2-yl)-1H-pyrazolo[4,3-c]pyridineHCID 86707055(6-Ethylpyrazin-2-yl)-trimethyl-stannane

생성물 1

HCID 867070546-(6-Ethylpyrazin-2-yl)-1-(6-fluoro-2-pyridyl)pyrazolo[4,3-c]pyridine수율 41.3%

시약·촉매·용매 2

HCID 178418397HCID 178418397, 화합물촉매HCID 31374Dimethylacetamide용매

반응 조건

온도
150 °C

실험 절차

To a solution of 6-chloro-1-(6-fluoro-2-pyridyl)pyrazolo[4,3-c]pyridine (85 mg; 0.34 mmol) and tetrakis(triphenylphosphine)palladium (40 mg, 0.034 mmol) in N,N-dimethylacetamide; 2.0 mL was added (6-ethylpyrazin-2-yl)-trimethyl-stannane (185 mg, 0.684 mmol). The reaction was purged with N2 for 5 min then heated at 150° C. for 45 min in biotage microwave. The reaction mixture was filtered through celite and concentrated. The crude product was diluted with EtOAc then washed with water. The organic layers was dried with sodium sulfate, filtered, and concentrated in vacuum. The crude product was purified by flash chromatography (EtOAc/Heptane eluted at 50% EtOAc) to give 6-(6-ethylpyrazin-2-yl)-1-(6-fluoro-2-pyridyl)pyrazolo[4,3-c]pyridine (45 mg) in 41% yield. MS (ESI) m/z: 321.2

후처리

  1. customThe reaction was purged with N2 for 5 min
  2. filtrationThe reaction mixture was filtered through celite
  3. concentrationconcentrated
  4. additionThe crude product was diluted with EtOAc
  5. washthen washed with water
  6. dry with materialThe organic layers was dried with sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated in vacuum
  9. customThe crude product was purified by flash chromatography (EtOAc/Heptane eluted at 50% EtOAc)

출처 및 근거

ORD 기록
ord-e906e0df7413481c9589cdf8d984c21b
출처 데이터셋
uspto-grants-2016_09
특허 번호
US09434725B2

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