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

HRID 2203306ノート

反応式

HRID 2203306 の反応式
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]

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-c89b665b907e4d389f7af17609d441c4
出典データセット
uspto-grants-2016_06
特許番号
US09365574B2

反応ノート

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