3-Bromoquinoline → (5-Oxo-5-quinolin-3-yl-pentyl)-carbamic acid tert-butyl ester

HRID 1837918노트

반응식

HRID 1837918 반응식
Br[C:2]1[CH:3]=[N:4][C:5]2[C:10]([CH:11]=1)=[CH:9][CH:8]=[CH:7][CH:6]=2.[Li]CCCC.[C:17]([O:21][C:22](=[O:34])[NH:23][CH2:24][CH2:25][CH2:26][CH2:27][C:28](=[O:33])N(OC)C)([CH3:20])([CH3:19])[CH3:18]>C(OCC)C>[C:17]([O:21][C:22](=[O:34])[NH:23][CH2:24][CH2:25][CH2:26][CH2:27][C:28](=[O:33])[C:2]1[CH:3]=[N:4][C:5]2[C:10]([CH:11]=1)=[CH:9][CH:8]=[CH:7][CH:6]=2)([CH3:20])([CH3:18])[CH3:19]

참가 물질

5

반응물 3

HCID 214133-BromoquinolineHCID 17958956Tert-butyl (5-(methoxy(methyl)amino)-5-oxopentyl)carbamateHCID 178418339Butyllithium

생성물 1

HCID 53998977(5-Oxo-5-quinolin-3-yl-pentyl)-carbamic acid tert-butyl ester

시약·촉매·용매 1

HCID 3283Diethyl Ether용매2회

실험 절차

To a stirred solution of 3-bromoquinoline (25 g, 120 mmol) in diethyl ether −78° C. was added nBuLi (2.5M THF, 48 ml, 120 mmol) dropwise over 30 minutes. After 30 minutes, 21-2 (3.9 g, 15 mmol), dissolved in 50 ml ether was added dropwise over 10 minutes. After 30 minutes, the cooling bath was removed. After 1.0 hour, the reaction was quenched with sat. NH4Cl. The organic portion was separated, washed with brine, dried (MgSO4) and concentrated. The residue was chromatographed (silica gel, 20-50% ethyl acetate/hexanes) to give 21-3 as a yellow solid.

후처리

  1. additionwas added dropwise over 10 minutes
  2. waitAfter 30 minutes
  3. customthe cooling bath was removed
  4. waitAfter 1.0 hour
  5. customthe reaction was quenched with sat. NH4Cl
  6. customThe organic portion was separated
  7. washwashed with brine
  8. dry with materialdried (MgSO4)
  9. concentrationconcentrated
  10. customThe residue was chromatographed (silica gel, 20-50% ethyl acetate/hexanes)

출처 및 근거

ORD 기록
ord-cdd20a98e2384b6da484218c245552a1
출처 데이터셋
uspto-grants-2004_08
특허 번호
US06784190B2

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