Sodium hydride → 2-Bromo-3-cyano-4-(4-phenylpiperidinyl)pyridine

HRID 587627ノート

反応式

HRID 587627 の反応式
[H-].[Na+].[C:3]1([CH:9]2[CH2:14][CH2:13][NH:12][CH2:11][CH2:10]2)[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[Br:15][C:16]1[N:23]=[CH:22][CH:21]=[C:20](Br)[C:17]=1[C:18]#[N:19]>CN(C=O)C>[Br:15][C:16]1[C:17]([C:18]#[N:19])=[C:20]([N:12]2[CH2:11][CH2:10][CH:9]([C:3]3[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=3)[CH2:14][CH2:13]2)[CH:21]=[CH:22][N:23]=1

参加物

5

反応物 3

HCID 24758Sodium hydrideHCID 698734-PhenylpiperidineHCID 574595912,4-Dibromopyridine-3-carbonitrile

生成物 1

HCID 574595942-Bromo-3-cyano-4-(4-phenylpiperidinyl)pyridine収率 95.4%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
0 °C

実験手順

To a suspension of NaH (0.146 g, 3.818 mmol, 60%) in DMF (20 ml) cooled at 0° C. was added 4-phenylpiperidine (0.616 g, 3.818 mmol). The resulting mixture was stirred for 5 min., then compound D1 (1 g, 3.016 mmol) was added. The resulting reaction mixture was stirred for 1 h. The reaction mixture was then quenched with NH4Cl (aqueous sat. solution) and extracted with Et2O. The organic layer was separated, dried (Na2SO4) and concentrated in vacuo. The crude product was purified by column chromatography (silica gel; DCM/7M solution of NH3 in MeOH gradient as eluent). The desired fractions were collected and concentrated in vacuo to yield intermediate compound D6 (0.985 g, 75%).

後処理

  1. customThe resulting reaction mixture
  2. stirringwas stirred for 1 h
  3. customThe reaction mixture was then quenched with NH4Cl (aqueous sat. solution)
  4. extractionextracted with Et2O
  5. customThe organic layer was separated
  6. dry with materialdried (Na2SO4)
  7. concentrationconcentrated in vacuo
  8. customThe crude product was purified by column chromatography (silica gel; DCM/7M solution of NH3 in MeOH gradient as eluent)
  9. customThe desired fractions were collected
  10. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-5a0c138a2ad7453b9c8ba5e2182b1e85
出典データセット
uspto-grants-2016_01
特許番号
US09226930B2

反応ノート

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