Water → 1-[8-Chloro-2-(4-fluorophenyl)imidazo[1,2-a]pyridin-3-yl]-2-propyn-1-one

HRID 456691

반응식

HRID 456691 반응식
[Cl:1][C:2]1[C:3]2[N:4]([C:8]([CH:18]=[O:19])=[C:9]([C:11]3[CH:16]=[CH:15][C:14]([F:17])=[CH:13][CH:12]=3)[N:10]=2)[CH:5]=[CH:6][CH:7]=1.[C:20]([Mg]Br)#[CH:21].O>O1CCCC1.ClCCl.[O-2].[O-2].[Mn+4]>[Cl:1][C:2]1[C:3]2[N:4]([C:8]([C:18](=[O:19])[C:20]#[CH:21])=[C:9]([C:11]3[CH:16]=[CH:15][C:14]([F:17])=[CH:13][CH:12]=3)[N:10]=2)[CH:5]=[CH:6][CH:7]=1

참가 물질

7

반응물 3

HCID 962WaterHCID 866010138-Chloro-2-(4-fluorophenyl)imidazo[1,2-a]pyridine-3-carboxaldehydeHCID 178418486HCID 178418486, 화합물

생성물 1

HCID 866010141-[8-Chloro-2-(4-fluorophenyl)imidazo[1,2-a]pyridin-3-yl]-2-propyn-1-one수율 55%

시약·촉매·용매 3

HCID 178418406HCID 178418406, 화합물촉매HCID 6344Dichloromethane용매HCID 8028Tetrahydrofuran용매

반응 조건

온도
-78 °C

실험 절차

To a cold (−78° C.) suspension of 8-chloro-2-(4-fluorophenyl)imidazo[1,2-α]pyridine-3-carbaldehyde (0.94 g, 3.42 mmol) in tetrahydrofuran (20 mL) was added ethynylmagnesium bromide (15 mL, 0.5 M in tetrahydrofuran, 7.5 mmol) dropwise. The reaction mixture was stirred at −78° C. for 1 hour, then at 0° C. for 2 hours. The resulting solution was poured into water and extracted with ethyl acetate. The organic layer was washed with water and brine and the combined organics were dried over magnesium sulfate. Filtration and concentration gave a white solid. This solid was dissolved in dichlormethane (60 mL) and to this solution was added manganese dioxide (10 g, 115 mmol). The reaction mixture was stirred at room temperature for 1 hour. The suspension was filtered through a pad of Celite and the filtrate was concentrated and purified by silica gel chromatography (1:1 hexanes:ethyl acetate) to give 1-[8-chloro-2-(4-fluorophenyl)imidazo[1,2-α]pyridin-3-yl]-2-propyn-1-one (0.56 g, 55%) as a white solid. 1H NMR (CDCl3) δ 9.67 (d, 1H), 7.68 (m, 3H), 7.12 (m, 3H), 2.89 (s, 1H); 19F NMR (CDCl3) δ −111.6; MS m/z 299 (M+1).

후처리

  1. waitat 0° C. for 2 hours
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with water and brine
  4. dry with materialthe combined organics were dried over magnesium sulfate
  5. filtrationFiltration and concentration
  6. customgave a white solid
  7. stirringThe reaction mixture was stirred at room temperature for 1 hour
  8. filtrationThe suspension was filtered through a pad of Celite
  9. concentrationthe filtrate was concentrated
  10. custompurified by silica gel chromatography (1:1 hexanes:ethyl acetate)

출처 및 근거

ORD 기록
ord-022b207ca15149c999dab7ad877bc35b
출처 데이터셋
uspto-grants-2007_03
특허 번호
US07186714B2

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