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

HRID 57877

反応式

HRID 57877 の反応式
[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

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 679Dimethyl Sulfoxide溶媒

反応条件

温度
95 °C

実験手順

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

後処理

  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)

出典と根拠

ORDレコード
ord-3d401b61bbcc445dbb22ecc949716f4e
出典データセット
uspto-grants-2016_09
特許番号
US09434725B2

関連ノート

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