Hexane → Ethyl 1-(5-bromo-3-pyridyl)-4-methyl-piperidine-4-carboxylate

HRID 712203ノート

反応式

HRID 712203 の反応式
Cl.[CH3:2][C:3]1([C:9]([OH:11])=[O:10])[CH2:8][CH2:7][NH:6][CH2:5][CH2:4]1.C([O-])([O-])=O.[Cs+].[Cs+].Br[C:19]1[CH:20]=[N:21][CH:22]=[C:23]([Br:25])[CH:24]=1.[CH3:26][CH2:27]CCCC>CS(C)=O>[Br:25][C:23]1[CH:24]=[C:19]([N:6]2[CH2:7][CH2:8][C:3]([CH3:2])([C:9]([O:11][CH2:26][CH3:27])=[O:10])[CH2:4][CH2:5]2)[CH:20]=[N:21][CH:22]=1

参加物

6

反応物 4

HCID 8058HexaneHCID 10796Cesium carbonateHCID 693693,5-DibromopyridineHCID 510003794-Methylpiperidine-4-carboxylic acid hydrochloride

生成物 1

HCID 66977152Ethyl 1-(5-bromo-3-pyridyl)-4-methyl-piperidine-4-carboxylate収率 14%

試薬・触媒・溶媒 1

HCID 679Dimethyl Sulfoxide溶媒

実験手順

To a solution of 4-methylpiperidine-4-carboxylate hydrochloride (3.6 g, 21.10 mmol) in DMSO (5 mL) was added Cs2CO3 (1.63 g, 5 mmol) at rt. The resulting mixture was stirred at rt for 10 min followed by addition of 3,5-dibromopyridine (1.0 g, 4.20 mmol). The reaction was heated up to 150° C. for 48 h. After completion (by TLC), the reaction mixture was poured into 100 mL of ice-cold water and extracted with EtOAc (3×100 mL). The combined organics were washed with brine, dried over anhydrous Na2SO4, filtered and evaporated under reduced pressure. The crude residue was purified over 100-200 M silica-gel by using 20.0% EtOAc:hexane to obtain a viscous liquid product (0.2 g, 14% yield). MS: 327.08 [M+H]+.

後処理

  1. temperatureThe reaction was heated up to 150° C. for 48 h
  2. extractionextracted with EtOAc (3×100 mL)
  3. washThe combined organics were washed with brine
  4. dry with materialdried over anhydrous Na2SO4
  5. filtrationfiltered
  6. customevaporated under reduced pressure
  7. customThe crude residue was purified over 100-200 M silica-gel

出典と根拠

ORDレコード
ord-8a8e40439d944a59bf726a063be720fb
出典データセット
uspto-grants-2015_11
特許番号
US09181234B2

反応ノート

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