Sodium hydride → 3-(4-benzyloxyphenyl)methyl-7-methyl-2-propyl-3H-imidazo[4,5-b]pyridine

HRID 2399447노트

반응식

HRID 2399447 반응식
[CH3:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]2[N:8]=[C:9]([CH2:11][CH2:12][CH3:13])[NH:10][C:3]=12.[H-].[Na+].[CH2:16]([O:23][C:24]1[CH:31]=[CH:30][C:27]([CH2:28]Cl)=[CH:26][CH:25]=1)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>CN(C=O)C>[CH2:16]([O:23][C:24]1[CH:25]=[CH:26][C:27]([CH2:28][N:8]2[C:4]3=[N:5][CH:6]=[CH:7][C:2]([CH3:1])=[C:3]3[N:10]=[C:9]2[CH2:11][CH2:12][CH3:13])=[CH:30][CH:31]=1)[C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1

참가 물질

5

반응물 3

HCID 24758Sodium hydrideHCID 700424-Benzyloxybenzyl chlorideHCID 150208527-Methyl-2-propyl-1H-imidazo[4,5-b]pyridine

생성물 1

HCID 193856923-(4-benzyloxyphenyl)methyl-7-methyl-2-propyl-3H-imidazo[4,5-b]pyridine수율 50.4%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

반응 조건

온도
0 °C

실험 절차

A suspension of 7-methyl-2-propylimidazo[4,5-b]pyridine (1.00 g, 5.71 mmol) and NaH (189 mg, 1.1 eq) in DMF (25 mL) was stirred for 1 hour and then cooled to 0° C. 4-Benzyloxybenzyl chloride (1.46 g; 1.1 eq) was then added and the ice bath removed. The reaction mixture was stirred for 2.5 hours and was then concentrated in vacuo. The residue was chromatographed on a silica gel flash chromatography column (30×200 mm) eluted with 30% ethyl acetate/hexane to yield 1.07 g (50%) of product.

후처리

  1. customthe ice bath removed
  2. stirringThe reaction mixture was stirred for 2.5 hours
  3. concentrationwas then concentrated in vacuo
  4. customThe residue was chromatographed on a silica gel flash chromatography column (30×200 mm)
  5. washeluted with 30% ethyl acetate/hexane

출처 및 근거

ORD 기록
ord-091fc7a32d2842ccabf10c3ef819582d
출처 데이터셋
uspto-grants-1995_09
특허 번호
US05449682

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