2-(Tributylstannyl)pyrazine → Tert-butyl 4-[6-(6-pyrazin-2-ylpyrazolo[4,3-c]pyridin-1-yl)-2-pyridyl]piperazine-1-carboxylate

HRID 57841

반응식

HRID 57841 반응식
Cl[C:2]1[N:7]=[CH:6][C:5]2[CH:8]=[N:9][N:10]([C:11]3[N:16]=[C:15]([N:17]4[CH2:22][CH2:21][N:20]([C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[CH2:19][CH2:18]4)[CH:14]=[CH:13][CH:12]=3)[C:4]=2[CH:3]=1.[N:30]1[CH:35]=[CH:34][N:33]=[CH:32][C:31]=1[Sn](CCCC)(CCCC)CCCC>CN(C)C(=O)C>[N:30]1[CH:35]=[CH:34][N:33]=[CH:32][C:31]=1[C:2]1[N:7]=[CH:6][C:5]2[CH:8]=[N:9][N:10]([C:11]3[N:16]=[C:15]([N:17]4[CH2:22][CH2:21][N:20]([C:23]([O:25][C:26]([CH3:28])([CH3:29])[CH3:27])=[O:24])[CH2:19][CH2:18]4)[CH:14]=[CH:13][CH:12]=3)[C:4]=2[CH:3]=1

참가 물질

4

반응물 2

HCID 27373162-(Tributylstannyl)pyrazineHCID 86707015Tert-butyl 4-[6-(6-chloropyrazolo[4,3-c]pyridin-1-yl)-2-pyridyl]piperazine-1-carboxylate

생성물 1

HCID 86707045Tert-butyl 4-[6-(6-pyrazin-2-ylpyrazolo[4,3-c]pyridin-1-yl)-2-pyridyl]piperazine-1-carboxylate수율 68.2%

시약·촉매·용매 1

HCID 31374Dimethylacetamide용매

반응 조건

온도
150 °C

실험 절차

A solution of tert-butyl 4-[6-(6-chloropyrazolo[4,3-c]pyridin-1-yl)-2-pyridyl]piperazine-1-carboxylate (40 mg, 0.096 mmol) and palladium(0)tetrakis(triphenylphosphine) (11 mg, 0.0095 mmol) in N,N-dimethylacetamide 1 mL was added (2-pyrazinyl)tributyltin (0.064 mL, 0.19 mmol). The reaction mixture 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 20% EtOAc) to give tert-butyl 4-[6-(6-pyrazin-2-ylpyrazolo[4,3-c]pyridin-1-yl)-2-pyridyl]piperazine-1-carboxylate 30 mg 67% yield.

후처리

  1. filtrationThe reaction mixture was filtered through celite
  2. concentrationconcentrated
  3. additionThe crude product was diluted with EtOAc
  4. washthen washed with water
  5. dry with materialThe organic layers was dried with sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuum
  8. customThe crude product was purified by flash chromatography (EtOAc/Heptane eluted at 20% EtOAc)

출처 및 근거

ORD 기록
ord-2d095c942d9e4872930c9e0b4bb48297
출처 데이터셋
uspto-grants-2016_09
특허 번호
US09434725B2

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