2-Iodoquinoline → HCID 58017288, 화합물

HRID 661572

반응식

HRID 661572 반응식
I[C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1.C([Mg]Cl)(C)C.[C:17]([O:21][C:22]([N:24]1[CH2:29][CH2:28][C:27]([CH:33]=[O:34])([CH2:30][CH2:31][CH3:32])[CH2:26][CH2:25]1)=[O:23])([CH3:20])([CH3:19])[CH3:18]>C1COCC1>[C:17]([O:21][C:22]([N:24]1[CH2:29][CH2:28][C:27]([CH:33]([OH:34])[C:2]2[CH:11]=[CH:10][C:9]3[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=3)[N:3]=2)([CH2:30][CH2:31][CH3:32])[CH2:26][CH2:25]1)=[O:23])([CH3:19])([CH3:20])[CH3:18]

참가 물질

5

반응물 3

HCID 810442-IodoquinolineHCID 58017246Tert-butyl 4-formyl-4-propylpiperidine-1-carboxylateHCID 178418918HCID 178418918, 화합물

생성물 1

HCID 58017288HCID 58017288, 화합물수율 19%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

반응 조건

온도
0 °C

실험 절차

To a solution of 2-iodoquinoline (670 mg, 2.6 mmol) in THF (10 mL) at 0° C. was slowly added isopropyl magnesium chloride (2.0 M in THF, 1.6 mL, 3.2 mmol). The reaction mixture was stirred at 0° C. for 30 minutes, then a solution of 4-formyl-4-propyl-piperidine-1-carboxylic acid tert-butyl ester (670 mg, 2.6 mmol) in THF (3 mL) was slowly added. The reaction mixture was stirred at 0° C. for 30 minutes, then warmed to room temperature, quenched with saturated aqueous NH4Cl solution, and extracted with EtOAc. The combined organic extracts were washed with brine, dried over MgSO4, filtered and concentrated under reduced pressure. The residue was purified by flash chromatography (0% to 20% EtOAc in hexanes) to afford 190 mg (19%) of 4-(hydroxy-quinolin-2-yl-methyl)-4-propyl-piperidine-1-carboxylic acid tert-butyl ester as a yellow oil.

후처리

  1. customat 0° C.
  2. stirringThe reaction mixture was stirred at 0° C. for 30 minutes
  3. temperaturewarmed to room temperature
  4. customquenched with saturated aqueous NH4Cl solution
  5. extractionextracted with EtOAc
  6. washThe combined organic extracts were washed with brine
  7. dry with materialdried over MgSO4
  8. filtrationfiltered
  9. concentrationconcentrated under reduced pressure
  10. customThe residue was purified by flash chromatography (0% to 20% EtOAc in hexanes)

출처 및 근거

ORD 기록
ord-c9201f90e68042faa3104c7b9bfe720a
출처 데이터셋
uspto-grants-2011_12
특허 번호
US08084623B2

연결된 노트

불러오는 중…