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

反応式

HRID 57856 の反応式
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]

参加物

5

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 178418397HCID 178418397、化合物触媒HCID 31374Dimethylacetamide溶媒

反応条件

温度
150 °C

実験手順

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

後処理

  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)

出典と根拠

ORDレコード
ord-e906e0df7413481c9589cdf8d984c21b
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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