p-Fluoronitrobenzene → Methyl 5-(4-nitrophenoxy)pyridine-3-carboxylate

HRID 13501

反応式

HRID 13501 の反応式
[CH3:1][O:2][C:3]([C:5]1[CH:6]=[N:7][CH:8]=[C:9]([OH:11])[CH:10]=1)=[O:4].C[Si]([N-][Si](C)(C)C)(C)C.[K+].F[C:23]1[CH:28]=[CH:27][C:26]([N+:29]([O-:31])=[O:30])=[CH:25][CH:24]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[CH3:1][O:2][C:3]([C:5]1[CH:6]=[N:7][CH:8]=[C:9]([O:11][C:23]2[CH:28]=[CH:27][C:26]([N+:29]([O-:31])=[O:30])=[CH:25][CH:24]=2)[CH:10]=1)=[O:4]

参加物

6

反応物 4

HCID 9590p-FluoronitrobenzeneHCID 11430Potassium CarbonateHCID 354317Methyl 5-hydroxypyridine-3-carboxylateHCID 3251421Potassium bis(trimethylsilyl)amide

生成物 1

HCID 22040734Methyl 5-(4-nitrophenoxy)pyridine-3-carboxylate

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
80 °C

実験手順

The mixture containing methyl-5-hydroxypyridine-3-carboxylate (1 eq), Potassium bis(trimethylsilyl)amide (1.2 eq) was stirred in N,N-dimethylformamide for 2 hours at room temperature. To this mixture was added 1-fluoro-4-nitrobenzene (1.1 eq) and Potassium carbonate (1.2 eq) and stirred at 80° C. for 16 h. The reaction mixture was then concentrated and partitioned between ethyl acetate and water. The organic layer was separated and washed with brine, dried, filtered and concentrated in vacuum to give brown solid. Purification on silica gel methyl-5-(4-nitrophenoxy)pyridine-3-carboxylate. MS: MH+=274.

後処理

  1. concentrationThe reaction mixture was then concentrated
  2. custompartitioned between ethyl acetate and water
  3. customThe organic layer was separated
  4. washwashed with brine
  5. customdried
  6. filtrationfiltered
  7. concentrationconcentrated in vacuum
  8. customto give brown solid
  9. customPurification on silica gel methyl-5-(4-nitrophenoxy)pyridine-3-carboxylate

出典と根拠

ORDレコード
ord-827bc1173d3441568cf390f6559fafd8
出典データセット
uspto-grants-2010_06
特許番号
US07728010B2

関連ノート

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