1H-Imidazole-4-carbaldehyde → HCID 59728099、化合物

HRID 2043350

反応式

HRID 2043350 の反応式
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([NH:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[C:19]([Br:23])[N:18]=2)[CH:12]=[CH:13][CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH:24]([C:26]1[N:27]=[CH:28][NH:29][CH:30]=1)=O.C([BH3-])#N.[Na+]>CO.[Cl-].[Zn+2].[Cl-]>[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([N:15]([CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[C:19]([Br:23])[N:18]=2)[CH2:24][C:26]2[NH:27][CH:28]=[N:29][CH:30]=2)[CH:12]=[CH:13][CH:14]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

参加物

6

反応物 3

HCID 764281H-Imidazole-4-carbaldehydeHCID 5003444Sodium cyanoborohydrideHCID 86620293(3-Benzyloxy-phenyl)-(6-bromo-pyridin-2-ylmethyl)-amine

生成物 1

HCID 59728099HCID 59728099、化合物収率 94%

試薬・触媒・溶媒 2

HCID 3007855Zincchloride触媒HCID 887Methanol溶媒

反応条件

温度
40 °C

実験手順

(3-Benzyloxy-phenyl)-(6-bromo-pyridin-2-ylmethyl)-amine (0.10 g, 0.27 mmol) was dissolved in methanol (2 ml). Then 4-formylimidazole (0.13 g, 1.35 mmol), zinc chloride (0.15 g, 1.08 mmol) and sodium cyanoborohydride (0.05 g, 0.81 mmol) were added and the reaction mixture was allowed to stir at 40° C. overnight. After cooling, the reaction mixture was poured onto ammoniumchloride/ice and extracted with ethyl acetate (2 times 50 ml). The organic layer was dried over magnesium sulfate and evaporated. The residue was purified using flash chromatography (SiO2; eluent: methanol/dichloromethane=1:9) to yield an off-white gum (0.11 g, 94%); MS (ISP): 451.1 ([81Br M+H]+), 449.1 ([79Br M+H]+).

後処理

  1. temperatureAfter cooling
  2. additionthe reaction mixture was poured onto ammoniumchloride/ice
  3. extractionextracted with ethyl acetate (2 times 50 ml)
  4. dry with materialThe organic layer was dried over magnesium sulfate
  5. customevaporated
  6. customThe residue was purified

出典と根拠

ORDレコード
ord-8ed97e996e29403eb9a6aa0b5145949f
出典データセット
uspto-grants-2013_11
特許番号
US08586617B2

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