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

HRID 57841

反応式

HRID 57841 の反応式
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

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 31374Dimethylacetamide溶媒

反応条件

温度
150 °C

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-2d095c942d9e4872930c9e0b4bb48297
出典データセット
uspto-grants-2016_09
特許番号
US09434725B2

関連ノート

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