Methyl iodide → 3-Bromo-5-(2-methoxypropan-2-yl)pyridine

HRID 712687ノート

反応式

HRID 712687 の反応式
[H-].[Na+].[Br:3][C:4]1[CH:5]=[C:6]([C:10]([OH:13])([CH3:12])[CH3:11])[CH:7]=[N:8][CH:9]=1.I[CH3:15]>CN(C=O)C>[Br:3][C:4]1[CH:9]=[N:8][CH:7]=[C:6]([C:10]([O:13][CH3:15])([CH3:11])[CH3:12])[CH:5]=1

参加物

5

反応物 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 223919662-(5-Bromo-3-pyridyl)propan-2-ol

生成物 1

HCID 667881343-Bromo-5-(2-methoxypropan-2-yl)pyridine収率 69.8%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒2 回

反応条件

温度
0 °C

実験手順

To a mixture of NaH (240 mg, 6.02 mmol) in DMF (dry, 4 mL) at 0° C. is added the solution of 2-(5-bromo-pyridin-3-yl)-propan-2-ol (500 mg, 2.31 mmol) in DMF (dry, 4 mL). The mixture is stirred at 0° C. for 15 min then raised to room temperature and stirred for 1 h. The mixture is then cooled back to 0° C. and iodomethane (397 mg, 2.80 mmol) iss added. The reaction mixture is stirred at room temperature overnight and is quenched by adding water dropwise. The mixture is partitioned between DCM and water. The DCM phase is separated and then washed with water twice. The DCM phase is evaporated under high vacuum. The residue is separated by silica gel flash column (EtOAc/Hepane 0 to 40% gradient, then 40%) to obtain 371 mg 3-bromo-5-(1-methoxy-1-methyl-ethyl)pyridine.

後処理

  1. temperaturethen raised to room temperature
  2. stirringstirred for 1 h
  3. temperatureThe mixture is then cooled back to 0° C.
  4. stirringThe reaction mixture is stirred at room temperature overnight
  5. customis quenched
  6. additionby adding water dropwise
  7. customThe mixture is partitioned between DCM and water
  8. customThe DCM phase is separated
  9. washwashed with water twice
  10. customThe DCM phase is evaporated under high vacuum
  11. customThe residue is separated by silica gel flash column (EtOAc/Hepane 0 to 40% gradient

出典と根拠

ORDレコード
ord-3af60b42a4b848ca8fb5e516774f8b2f
出典データセット
uspto-grants-2015_11
特許番号
US09181272B2

反応ノート

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