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

HRID 456685노트

반응식

HRID 456685 반응식
[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

참가 물질

5

반응물 2

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

생성물 1

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

시약·촉매·용매 2

HCID 23925Iron촉매HCID 887Methanol용매2회

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-ae9679ebf79f4ee5b567661d24151925
출처 데이터셋
uspto-grants-2007_03
특허 번호
US07186714B2

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