Ammonium Chloride → 1-[8-Amino-2-(4-fluorophenyl)imidazo[1,2-a)pyridin-3-yl]ethanone

HRID 456685ノート

反応式

HRID 456685 の反応式
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]=[C:10]3[C:15]([N+:16]([O-])=O)=[CH:14][CH:13]=[CH:12][N:11]3[C:19]=2[C:20](=[O:22])[CH3:21])=[CH:4][CH:3]=1.[Cl-].[NH4+]>CO.[Fe]>[NH2:16][C:15]1[C:10]2[N:11]([C:19]([C:20](=[O:22])[CH3:21])=[C:8]([C:5]3[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=3)[N:9]=2)[CH:12]=[CH:13][CH:14]=1

参加物

5

反応物 2

HCID 25517Ammonium ChlorideHCID 695493021-[2-(4-Fluorophenyl)-8-nitroimidazo[1,2-a]pyridin-3-yl]ethanone

生成物 1

HCID 695497661-[8-Amino-2-(4-fluorophenyl)imidazo[1,2-a)pyridin-3-yl]ethanone収率 70.9%

試薬・触媒・溶媒 2

HCID 23925Iron触媒HCID 887Methanol溶媒2 回

実験手順

A solution of 1-[2-(4-fluorophenyl)-8-nitroimidazo[1,2-α]pyridin-3-yl]ethanone (100 mg, 0.33 mmol) in methanol (3 mL) was added to a suspension of iron (93 mg, 1.7 mmol) and ammonium chloride (149 mg, 2.8 mmol) in aqueous methanol. This reaction mixture was heated to reflux for 10 hours. The reaction mixture was filtered and the filtrate concentrated under reduced pressure to a solid. This solid was purified by silica gel chromatography (5% methanol in dichloromethane) to give 63 mg (70%) of 1-[8-amino-2-(4-fluorophenyl)imidazo[1,2-α]pyridin-3-yl]ethanone as a foam. 1H NMR (CDCl3): δ 9.21 (d, 1H), 7.61 (m, 2H), 7.25 (m, 2H), 6.94 (t, 1H) 6.72 (d, 1H), 4.63 (broad s, 2H), 2.19 (s, 3H); MS m/z 270 (M+1).

後処理

  1. temperatureThis reaction mixture was heated
  2. temperatureto reflux for 10 hours
  3. filtrationThe reaction mixture was filtered
  4. concentrationthe filtrate concentrated under reduced pressure to a solid
  5. customThis solid was purified by silica gel chromatography (5% methanol in dichloromethane)

出典と根拠

ORDレコード
ord-ae9679ebf79f4ee5b567661d24151925
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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