3-Bromo-5-methoxypyridine → 5-Bromo-2-ethoxy-3-methoxypyridine

HRID 39357

反応式

HRID 39357 の反応式
[Br:1][C:2]1[CH:3]=[C:4]([O:9][CH3:10])[C:5](Cl)=[N:6][CH:7]=1.BrC1C=N[CH:15]=[C:16]([O:18]C)C=1.[O-]CC.[Na+].C(O)C>O>[Br:1][C:2]1[CH:3]=[C:4]([O:9][CH3:10])[C:5]([O:18][CH2:16][CH3:15])=[N:6][CH:7]=1

参加物

5

反応物 3

HCID 8171633-Bromo-5-methoxypyridineHCID 167481085-Bromo-2-chloro-3-methoxypyridineHCID 23706232Ethanol sodium ethoxide

生成物 1

HCID 666174235-Bromo-2-ethoxy-3-methoxypyridine

試薬・触媒・溶媒 1

HCID 962Water溶媒

実験手順

As shown in step 5-i of Scheme 5, 5-bromo-2-chloro-3-methoxypyridine (1.0 g, 4.5 mmol, prepared in the same manner as Compound 1003 in Example 2 starting with 3-bromo-5-methoxypyridine) was treated with a sodium ethoxide/ethanol solution (5.05 mL, 21% w/v, 13.5 mmol) and the reaction mixture microwave irradiated at 100° C. for 20 minutes. Water was added and the ethanol evaporated under reduced pressure. The resulting aqueous solution was extracted with DCM and ether, followed by drying the combined extracts over MgSO4. After filtration, removal of the volatiles under reduced pressure provided 5-bromo-2-ethoxy-3-methoxypyridine (Compound 1016), 0.72 g, 69% yield): ESMS (M+H) 232.32/234.23. As shown in step 5-ii of Scheme 5, Compound 1017 (ESMS (M+H) 218.32/220.23) was prepared in the same manner as Compound 1016, using sodium methoxide in methanol instead of sodium ethoxide in ethanol.

後処理

  1. customthe reaction mixture microwave irradiated at 100° C. for 20 minutes
  2. customthe ethanol evaporated under reduced pressure
  3. extractionThe resulting aqueous solution was extracted with DCM and ether
  4. dry with materialby drying the combined extracts over MgSO4
  5. filtrationAfter filtration, removal of the volatiles under reduced pressure

出典と根拠

ORDレコード
ord-86dc72dd18ba4196a544d017b0c63b17
出典データセット
uspto-grants-2013_09
特許番号
US08524906B2

関連ノート

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