Magnesium perchlorate → Methyl 2-bromo-2-(pyridin-2-yl)propanoate

HRID 2203306노트

반응식

HRID 2203306 반응식
Cl([O-])(=O)(=O)=O.[Mg+2].Cl([O-])(=O)(=O)=O.[N:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[CH:18]([CH3:23])[C:19]([O:21][CH3:22])=[O:20].[Br:24]N1C(=O)CCC1=O>C(#N)C>[Br:24][C:18]([C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][N:12]=1)([CH3:23])[C:19]([O:21][CH3:22])=[O:20]

참가 물질

5

반응물 3

HCID 24840Magnesium perchlorateHCID 67184N-bromobutanimideHCID 54595201Methyl 2-(pyridin-2-yl)propanoate

생성물 1

HCID 67991933Methyl 2-bromo-2-(pyridin-2-yl)propanoate

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

Magnesium perchlorate (0.46 g, 2.08 mmol) was added to an acetonitrile (18 mL) solution containing the intermediate from Step A (1.04 g, 6.30 mmol). After stirring for 5 minutes N-bromosuccinimide (1.35 g, 7.55 mmol) was added and the reaction solution was stirred overnight. The solution was then partitioned between EtOAc and 1N NaHCO3 aq. The organic layer was washed with brine, dried over MgSO4, filtered and concentrated. The residue was purified by silica gel chromatography using a hexanes/EtOAc gradient to give the indicated product. 1H NMR (400 MHz, CH3CN-d3): δ 8.48 (d, J=4.8 Hz, 1H); 7.85-736 (m, 2H); 7.32-7.26 (m, 1H); 3.72 (s, 3H); 2.24 (s, 3H). m/z=244.4 (M+H).

후처리

  1. additionwas added
  2. customThe solution was then partitioned between EtOAc and 1N NaHCO3 aq. The organic layer
  3. washwas washed with brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified by silica gel chromatography
  8. customto give the indicated product

출처 및 근거

ORD 기록
ord-c89b665b907e4d389f7af17609d441c4
출처 데이터셋
uspto-grants-2016_06
특허 번호
US09365574B2

반응 노트

불러오는 중…