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

HRID 1428488노트

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HRID 1428488 반응식
[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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

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온도
0 °C

실험 절차

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%).

후처리

  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

출처 및 근거

ORD 기록
ord-008bd79b5c9f47d3bf2f693777310335
출처 데이터셋
uspto-grants-2015_01
특허 번호
US08937060B2

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