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 539766노트

반응식

HRID 539766 반응식
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]

참가 물질

5

반응물 2

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

생성물 1

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

시약·촉매·용매 2

HCID 887Methanol용매HCID 79724-Methylmorpholine용매

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온도
220 °C

실험 절차

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]+.

후처리

  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)

출처 및 근거

ORD 기록
ord-51fba795de2c48adb0dc1048a00f8d98
출처 데이터셋
uspto-grants-2014_10
특허 번호
US08871767B2

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