2-Bromo-6-fluoropyridine → tert-butyl N-[1-(6-bromo-2-pyridyl)-6-methyl-3-piperidyl]carbamate

HRID 57877

반응식

HRID 57877 반응식
[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4](F)[N:3]=1.[CH3:9][CH:10]1[NH:15][CH2:14][CH:13]([NH:16][C:17](=[O:23])[O:18][C:19]([CH3:22])([CH3:21])[CH3:20])[CH2:12][CH2:11]1>CS(C)=O>[Br:1][C:2]1[N:3]=[C:4]([N:15]2[CH:10]([CH3:9])[CH2:11][CH2:12][CH:13]([NH:16][C:17](=[O:23])[O:18][C:19]([CH3:22])([CH3:21])[CH3:20])[CH2:14]2)[CH:5]=[CH:6][CH:7]=1

참가 물질

4

반응물 2

HCID 6394382-Bromo-6-fluoropyridineHCID 42609251tert-butyl N-(6-methylpiperidin-3-yl)carbamate

생성물 1

HCID 86707072tert-butyl N-[1-(6-bromo-2-pyridyl)-6-methyl-3-piperidyl]carbamate수율 39%

시약·촉매·용매 1

HCID 679Dimethyl Sulfoxide용매

반응 조건

온도
95 °C

실험 절차

A solution containing 2-bromo-6-fluoropyridine (0.95 mL, 6.65 mmol and tert-butyl 6-methylpiperidin-3-ylcarbamate (750 mg, 3.32 mmol) in methyl sulfoxide 5.0 ml was heated 95° C. 18 h. The reaction was quenched with water then extracted with EtOAc. The organic layers was dried with sodium sulfate, filtered, and concentrated in vacuum. The crude product was purified by flash chromatography (EtOAc/Heptane eluted at 30% EtOAc) to give tert-butyl N-[1-(6-bromo-2-pyridyl)-6-methyl-3-piperidyl]carbamate (480 mg) in 39% yield. MS (ESI) m/z: 371.2

후처리

  1. custom18 h
  2. customThe reaction was quenched with water
  3. extractionthen extracted with EtOAc
  4. dry with materialThe organic layers was dried with sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuum
  7. customThe crude product was purified by flash chromatography (EtOAc/Heptane eluted at 30% EtOAc)

출처 및 근거

ORD 기록
ord-3d401b61bbcc445dbb22ecc949716f4e
출처 데이터셋
uspto-grants-2016_09
특허 번호
US09434725B2

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