1H-Imidazole-4-carbaldehyde → HCID 59728099, 화합물

HRID 2043350

반응식

HRID 2043350 반응식
[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

참가 물질

6

반응물 3

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

생성물 1

HCID 59728099HCID 59728099, 화합물수율 94%

시약·촉매·용매 2

HCID 3007855Zincchloride촉매HCID 887Methanol용매

반응 조건

온도
40 °C

실험 절차

(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]+).

후처리

  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

출처 및 근거

ORD 기록
ord-8ed97e996e29403eb9a6aa0b5145949f
출처 데이터셋
uspto-grants-2013_11
특허 번호
US08586617B2

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