1,3-Dichloroacetone → 2-(chloromethyl)-5-methylimidazo[1,2-a]pyridine

HRID 1842431노트

반응식

HRID 1842431 반응식
[Cl:1][CH2:2][C:3]([CH2:5]Cl)=O.[CH3:7][C:8]1[N:13]=[C:12]([NH2:14])[CH:11]=[CH:10][CH:9]=1>C(#N)C>[Cl:1][CH2:2][C:3]1[N:14]=[C:12]2[CH:11]=[CH:10][CH:9]=[C:8]([CH3:7])[N:13]2[CH:5]=1

참가 물질

4

반응물 2

HCID 107931,3-DichloroacetoneHCID 157652-Amino-6-methylpyridine

생성물 1

HCID 9576122-(chloromethyl)-5-methylimidazo[1,2-a]pyridine수율 70.7%

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

1,3-Dichloroacetone (17.6 g, 138.3 mmol) was added to a solution of 6-methylpyridin-2-amine (10 g, 92.5 mmol) in acetonitrile (200 ml). The mixture was heated at reflux for 14 h (the reaction was monitored by TLC). The mixture was concentrated under reduced pressure, the residue was diluted with water, and the pH was adjusted to 7.5 with sodium bicarbonate solution. The mixture was extracted with EtOAc, the combined organics were dried over sodium sulfate, filtered and concentrated under reduced pressure. The residue was purified by flash column chromatography using 10% ethyl acetate in n-hexane and silica gel (230-400 mesh) to afford 2-(chloromethyl)-5-methylimidazo[1,2-a]pyridine (7.0 g, 70.7%,) as a pale yellow solid. 1H NMR: 200 MHz, CDCl3: δ 8.15 (s, 1H), 7.6 (dd, 2H), 7.1 (t, 1H), 6.8 (t, 1H), 4.95 (s, 2H), 2.6 (s, 3H). MS: [M+H]+: m/z=181.5.

후처리

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 14 h (the reaction
  3. concentrationThe mixture was concentrated under reduced pressure
  4. additionthe residue was diluted with water
  5. extractionThe mixture was extracted with EtOAc
  6. dry with materialthe combined organics were dried over sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure
  9. customThe residue was purified by flash column chromatography

출처 및 근거

ORD 기록
ord-ce3fa98e82264417813df0c2e33c88dd
출처 데이터셋
uspto-grants-2015_02
특허 번호
US08946222B2

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