Methyl iodide → Methyl 6-bromo-4-iodonicotinate

HRID 1502400ノート

反応式

HRID 1502400 の反応式
[Br:1][C:2]1[CH:10]=[C:9]([I:11])[C:5]([C:6]([OH:8])=[O:7])=[CH:4][N:3]=1.[C:12](=O)([O-])[O-].[K+].[K+].CI>CN(C)C=O.C(OCC)(=O)C>[Br:1][C:2]1[CH:10]=[C:9]([I:11])[C:5]([C:6]([O:8][CH3:12])=[O:7])=[CH:4][N:3]=1

参加物

6

反応物 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 582662986-Bromo-4-iodonicotinic acid

生成物 1

HCID 86674963Methyl 6-bromo-4-iodonicotinate収率 83%

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
60 °C

実験手順

A mixture of 6-bromo-4-iodonicotinic acid (75 mg, 0.23 mmol), potassium carbonate (63 mg, 0.46 mmol), and methyl iodide (0.017 mL, 0.27 mmol) in N,N-dimethylformamide (0.5 mL) was heated at 60° C. for 30 minutes. The cooled reaction mixture was diluted with ethyl acetate (20 mL) and washed with water (15 mL). The organic layer was separated, dried over sodium sulfate, filtered, and evaporated in vacuo to afford a residue that was purified by flash chromatography (silica, 4 g, ISCO, 0-50% ethyl acetate in heptane) to afford the title compound as a white solid (65 mg, 83%), which was used in the next step without further purification.

後処理

  1. customThe cooled reaction mixture
  2. washwashed with water (15 mL)
  3. customThe organic layer was separated
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. customevaporated in vacuo
  7. customto afford a residue that
  8. customwas purified by flash chromatography (silica, 4 g, ISCO, 0-50% ethyl acetate in heptane)

出典と根拠

ORDレコード
ord-35f745f8d0d14f11bd62fa0c65f1577e
出典データセット
uspto-grants-2015_12
特許番号
US09206175B2

反応ノート

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