4-Methoxybenzyl alcohol → 5-Bromo-4-ethoxy-2-((4-methoxybenzyl)oxy)pyridine

HRID 1050107노트

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HRID 1050107 반응식
[Br:1][C:2]1[C:3]([O:9][CH2:10][CH3:11])=[CH:4][C:5](Cl)=[N:6][CH:7]=1.C([O-])([O-])=O.[Cs+].[Cs+].[CH3:18][O:19][C:20]1[CH:25]=[CH:24][C:23]([CH2:26][OH:27])=[CH:22][CH:21]=1>CN(C=O)C>[Br:1][C:2]1[C:3]([O:9][CH2:10][CH3:11])=[CH:4][C:5]([O:27][CH2:26][C:23]2[CH:24]=[CH:25][C:20]([O:19][CH3:18])=[CH:21][CH:22]=2)=[N:6][CH:7]=1

참가 물질

5

반응물 3

HCID 77384-Methoxybenzyl alcoholHCID 10796Cesium carbonateHCID 707008775-Bromo-2-chloro-4-ethoxypyridine

생성물 1

HCID 904233545-Bromo-4-ethoxy-2-((4-methoxybenzyl)oxy)pyridine수율 37.2%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

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온도
120 °C

실험 절차

A mixture of 5-bromo-2-chloro-4-ethoxypyridine (8 g, 33.8 mmol), Cs2CO3 (33.1 g, 101 mmol) and (4-methoxyphenyl)methanol (5.37 g, 38.9 mmol) in DMF (100 mL) was stirred at 120° C. for 12 h. The mixture was then concentrated. The residue was added to DCM (150 mL). The mixture was filtered and the filtrate was concentrated. The crude material was purified by silica column chromatography (PE/EA=8:1). All fractions found to contain product by TLC (PE/EA=5:1, Rf=0.4) were combined and concentrated to yield a yellow solid of 5-bromo-4-ethoxy-2-((4-methoxybenzyl)oxy)pyridine (5 g, 12.57 mmol, 37% yield): 1H NMR (400 MHz, CDCl3) δ: 8.05 (s, 1H), 7.32 (d, J=8.8 Hz, 1H), 6.84 (d, J=8.4 Hz, 1H), 6.17 (s, 1H), 5.18 (s, 2H), 4.02 (q, J=6.8 Hz, 2H), 3.74 (s, 3H), 1.40 (t, J=7.2 Hz, 3H); ES-LCMS m/z 338 (M+H).

후처리

  1. concentrationThe mixture was then concentrated
  2. additionThe residue was added to DCM (150 mL)
  3. filtrationThe mixture was filtered
  4. concentrationthe filtrate was concentrated
  5. customThe crude material was purified by silica column chromatography (PE/EA=8:1)
  6. concentrationconcentrated

출처 및 근거

ORD 기록
ord-459cb4a2779b44caa609a57b11cadbf5
출처 데이터셋
uspto-grants-2016_07
특허 번호
US09382238B2

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