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

HRID 912446

反応式

HRID 912446 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 then cooled to room temperature and diluted with ethyl acetate before washing twice with 7M NH4OH. The organic layer was 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 the desired product (95% yield).

後処理

  1. customdegassed with nitrogen under vacuum
  2. temperatureThe mixture was then cooled to room temperature
  3. additiondiluted with ethyl acetate
  4. washbefore washing twice with 7M NH4OH
  5. washThe organic layer was 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-ef87d3111f4a4fe6b6a4759631c1b811
出典データセット
uspto-grants-2011_09
特許番号
US08026233B2

関連ノート

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