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

HRID 456691ノート

反応式

HRID 456691 の反応式
[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

参加物

7

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 178418406HCID 178418406、化合物触媒HCID 6344Dichloromethane溶媒HCID 8028Tetrahydrofuran溶媒

反応条件

温度
-78 °C

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-022b207ca15149c999dab7ad877bc35b
出典データセット
uspto-grants-2007_03
特許番号
US07186714B2

反応ノート

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