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

HRID 1842431ノート

反応式

HRID 1842431 の反応式
[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

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-ce3fa98e82264417813df0c2e33c88dd
出典データセット
uspto-grants-2015_02
特許番号
US08946222B2

反応ノート

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