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

HRID 712203노트

반응식

HRID 712203 반응식
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

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 679Dimethyl Sulfoxide용매

실험 절차

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]+.

후처리

  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

출처 및 근거

ORD 기록
ord-8a8e40439d944a59bf726a063be720fb
출처 데이터셋
uspto-grants-2015_11
특허 번호
US09181234B2

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