Sodium cyanoborohydride → 8-(2-Ethyl-6-methylbenzylamino)-2,3,6-trimethylimidazo[1,2-a]pyridine

HRID 1386071ノート

反応式

HRID 1386071 の反応式
[NH2:1][C:2]1[C:3]2[N:4]([C:9]([CH3:13])=[C:10]([CH3:12])[N:11]=2)[CH:5]=[C:6]([CH3:8])[CH:7]=1.[CH2:14]([C:16]1[CH:23]=[CH:22][CH:21]=[C:20]([CH3:24])[C:17]=1[CH:18]=O)[CH3:15].C([BH3-])#N.[Na+]>CO.[Cl-].[Zn+2].[Cl-]>[CH2:14]([C:16]1[CH:23]=[CH:22][CH:21]=[C:20]([CH3:24])[C:17]=1[CH2:18][NH:1][C:2]1[C:3]2[N:4]([C:9]([CH3:13])=[C:10]([CH3:12])[N:11]=2)[CH:5]=[C:6]([CH3:8])[CH:7]=1)[CH3:15]

参加物

6

反応物 3

HCID 5003444Sodium cyanoborohydrideHCID 226726328-Amino-2,3,6-trimethylimidazo[1,2-a]pyridineHCID 229974692-Ethyl-6-methylbenzaldehyde

生成物 1

HCID 217173628-(2-Ethyl-6-methylbenzylamino)-2,3,6-trimethylimidazo[1,2-a]pyridine収率 33%

試薬・触媒・溶媒 2

HCID 3007855Zincchloride触媒HCID 887Methanol溶媒

実験手順

A stirred mixture of 8-amino-2,3,6-trimethylimidazo[1,2-a]pyridine (0.5 g, 2.8 mmol), 2-ethyl-6-methylbenzaldehyde (0.45 g, 3 mmol) and zinc(II)chloride (0.4 g, 3 mmol) in 50 ml methanol was treated with sodium cyanoborohydride (0.19 g, 3 mmol) and refluxed for 20 h. The methanol was evaporated under reduced pressure and the residue was dissolved in dichloromethylene and water. The organic layer was separated, dried over sodium sulfate and evaporated under reduced pressure. The residue was chromatographed on silicagel with dichloromethylene:methanol (10:1) which yielded 0.28 g (33%) of the title compound.

後処理

  1. temperaturerefluxed for 20 h
  2. customThe methanol was evaporated under reduced pressure
  3. dissolutionthe residue was dissolved in dichloromethylene
  4. customThe organic layer was separated
  5. dry with materialdried over sodium sulfate
  6. customevaporated under reduced pressure
  7. customThe residue was chromatographed on silicagel with dichloromethylene:methanol (10:1) which

出典と根拠

ORDレコード
ord-d0cff468a59141b48036f99aff1afe30
出典データセット
uspto-grants-2001_07
特許番号
US06265415B1

反応ノート

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