Dimethylacetamide → 5-(2,4-Difluorophenoxy)-1-isobutyl-1h-indazole-6-carbonitrile

HRID 909189

反応式

HRID 909189 の反応式
Br[C:2]1[CH:10]=[C:9]2[C:5]([CH:6]=[N:7][N:8]2[CH2:11][CH:12]([CH3:14])[CH3:13])=[CH:4][C:3]=1[O:15][C:16]1[CH:21]=[CH:20][C:19]([F:22])=[CH:18][C:17]=1[F:23].C[C:25]([N:27](C)C)=O>>[F:23][C:17]1[CH:18]=[C:19]([F:22])[CH:20]=[CH:21][C:16]=1[O:15][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][C:2]=1[C:25]#[N:27])[N:8]([CH2:11][CH:12]([CH3:14])[CH3:13])[N:7]=[CH:6]2

参加物

3

反応物 2

HCID 31374DimethylacetamideHCID 574187626-Bromo-5-(2,4-difluorophenoxy)-1-isobutyl-1H-indazole

生成物 1

HCID 426111415-(2,4-Difluorophenoxy)-1-isobutyl-1h-indazole-6-carbonitrile収率 95%

反応条件

温度
150 °C

実験手順

6-Bromo-5-(2,4-difluorophenoxy)-1-isobutyl-1H-indazole (31.2 g, 82 mmol) and Cu(I) CN (13.9 g, 156 mmol) were dissolved in DMA and degassed with nitrogen under vacuum. The reaction mixture was heated to 150° C. for 16 hours. The mixture was cooled to room temperature and diluted with ethyl acetate before washing twice with 7M NH4OH. The organics were washed with brine and degassed with nitrogen before being dried over MgSO4 and concentrated under reduced pressure. The crude product was chromatographed eluting with 10% ethyl acetate in hexanes to afford 25.1 g of product (95% yield).

後処理

  1. customdegassed with nitrogen under vacuum
  2. temperatureThe mixture was cooled to room temperature
  3. additiondiluted with ethyl acetate
  4. washbefore washing twice with 7M NH4OH
  5. washThe organics were washed with brine
  6. customdegassed with nitrogen
  7. dry with materialbefore being dried over MgSO4
  8. concentrationconcentrated under reduced pressure
  9. customThe crude product was chromatographed
  10. washeluting with 10% ethyl acetate in hexanes

出典と根拠

ORDレコード
ord-383e377be50b4e0ca8852198081220dc
出典データセット
uspto-grants-2011_09
特許番号
US08017641B2

関連ノート

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