1,2-Dibromoethane → Methyl 2-(2-bromoethyl)-1-oxo-1,2-dihydroisoquinoline-7-carboxylate

HRID 1616143노트

반응식

HRID 1616143 반응식
[H-].[Na+].[O:3]=[C:4]1[C:13]2[C:8](=[CH:9][CH:10]=[C:11]([C:14]([O:16][CH3:17])=[O:15])[CH:12]=2)[CH:7]=[CH:6][NH:5]1.[Br:18][CH2:19][CH2:20]Br>CN(C=O)C>[Br:18][CH2:19][CH2:20][N:5]1[CH:6]=[CH:7][C:8]2[C:13](=[CH:12][C:11]([C:14]([O:16][CH3:17])=[O:15])=[CH:10][CH:9]=2)[C:4]1=[O:3]

참가 물질

5

반응물 3

HCID 78391,2-DibromoethaneHCID 24758Sodium hydrideHCID 60075037Methyl 1-oxo-1,2-dihydroisoquinoline-7-carboxylate

생성물 1

HCID 67281903Methyl 2-(2-bromoethyl)-1-oxo-1,2-dihydroisoquinoline-7-carboxylate수율 38.3%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매2회

실험 절차

To a stirred suspension of sodium hydride (60% in mineral oil, 0.81 g, 20.2 mmol) in DMF (30 mL) under an atmosphere of nitrogen was added methyl 1-oxo-1,2-dihydroisoquinoline-7-carboxylate (2.05 g, 10.1 mmol) in DMF (20 mL) dropwise. The mixture was stirred for 30 mins, then 1,2-dibromoethane (8.7 mL, 101 mmol) was added quickly and the resulting solution was stirred for 2 h. The reaction was quenched with water and extracted with EtOAc (2×). The combined organic phases were then washed with water, and brine, dried over anhydrous Na2SO4, filtered and concentrated. The residue was purified by flash silica gel chromatography (0% to 40% EtOAc/hexanes) to afford methyl 2-(2-bromoethyl)-1-oxo-1,2-dihydroisoquinoline-7-carboxylate (1.20 g, 38%). LC-MS: (FA) ES+ 311.

후처리

  1. stirringthe resulting solution was stirred for 2 h
  2. customThe reaction was quenched with water
  3. extractionextracted with EtOAc (2×)
  4. washThe combined organic phases were then washed with water, and brine
  5. dry with materialdried over anhydrous Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe residue was purified by flash silica gel chromatography (0% to 40% EtOAc/hexanes)

출처 및 근거

ORD 기록
ord-ac1929eb2d37402fa8d65c328256f837
출처 데이터셋
uspto-grants-2014_07
특허 번호
US08765773B2

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