2-(3-Bromo-4-(trifluoromethyl)phenyl)-6-ethoxyimidazo[1,2-b]pyridazine → 5-(6-Ethoxyimidazo[2,1-f]pyridazin-2-yl)-2-(trifluoromethyl)benzonitrile

HRID 539766ノート

反応式

HRID 539766 の反応式
Br[C:2]1[CH:3]=[C:4]([C:12]2[N:13]=[C:14]3[N:19]([CH:20]=2)[N:18]=[C:17]([O:21][CH2:22][CH3:23])[CH:16]=[CH:15]3)[CH:5]=[CH:6][C:7]=1[C:8]([F:11])([F:10])[F:9].[C:24]([Cu])#[N:25]>CN1CCOCC1.CO>[CH2:22]([O:21][C:17]1[CH:16]=[CH:15][C:14]2=[N:13][C:12]([C:4]3[CH:5]=[CH:6][C:7]([C:8]([F:11])([F:10])[F:9])=[C:2]([CH:3]=3)[C:24]#[N:25])=[CH:20][N:19]2[N:18]=1)[CH3:23]

参加物

5

反応物 2

HCID 575162022-(3-Bromo-4-(trifluoromethyl)phenyl)-6-ethoxyimidazo[1,2-b]pyridazineHCID 178418546HCID 178418546、化合物

生成物 1

HCID 679824015-(6-Ethoxyimidazo[2,1-f]pyridazin-2-yl)-2-(trifluoromethyl)benzonitrile収率 71%

試薬・触媒・溶媒 2

HCID 887Methanol溶媒HCID 79724-Methylmorpholine溶媒

反応条件

温度
220 °C

実験手順

A mixture of 2-[3-bromo-4-(trifluoromethyl)phenyl]-6-ethoxy-imidazo[2,1-f]pyridazine (0.050 g, 0.129 mmol) and CuCN (0.058 g) in 4-methylmorpholine (2.0 mL) is heated in the microwave at 220° C. for 10 min. The mixture is diluted with MeOH (10 mL) and the solids are removed by filtration. The crude solution is concentrated to remove the MeOH. Water (50 mL) is added and the solid precipitate is collected. The crude product is purified by silica gel chromatography (0-100% EtOAc in Hexanes) to give the title compound (0.03 g, 71% yield). LCMS m/z=333.3 [M+H]+.

後処理

  1. customthe solids are removed by filtration
  2. concentrationThe crude solution is concentrated
  3. customto remove the MeOH
  4. additionWater (50 mL) is added
  5. customthe solid precipitate is collected
  6. customThe crude product is purified by silica gel chromatography (0-100% EtOAc in Hexanes)

出典と根拠

ORDレコード
ord-51fba795de2c48adb0dc1048a00f8d98
出典データセット
uspto-grants-2014_10
特許番号
US08871767B2

反応ノート

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