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

HRID 1050107ノート

反応式

HRID 1050107 の反応式
[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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
120 °C

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-459cb4a2779b44caa609a57b11cadbf5
出典データセット
uspto-grants-2016_07
特許番号
US09382238B2

反応ノート

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