N-bromobutanimide → Methyl 6-(bromomethyl)pyridine-2-carboxylate

HRID 1176757

反応式

HRID 1176757 の反応式
[CH3:1][O:2][C:3]([C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([CH3:11])[N:6]=1)=[O:4].C1C(=O)N([Br:19])C(=O)C1>C(Cl)(Cl)(Cl)Cl.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>[CH3:1][O:2][C:3]([C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([CH2:11][Br:19])[N:6]=1)=[O:4]

参加物

5

反応物 2

HCID 67184N-bromobutanimideHCID 73022Methyl 6-methylpyridine-2-carboxylate

生成物 1

HCID 21471714Methyl 6-(bromomethyl)pyridine-2-carboxylate収率 20.2%

試薬・触媒・溶媒 2

HCID 7187Benzoyl Peroxide触媒HCID 5943Carbon Tetrachloride溶媒

実験手順

6-Bromomethyl-pyridine-2-carboxylic acid methyl ester was prepared according to Wells, G. J. et al. (WO 94/11398): A mixture of 6-methyl-pyridine-2-carboxylic acid methyl ester (6.5 g, 43.0 mmol), benzoyl peroxide (25 mg, 0.1 mmol) and NBS (8.5 g, 47.8 mmol) in carbon tetrachloride (250 mL) was heated at reflux overnight. The reaction mixture was cooled to room temperature, filtered, evaporated, and purified by chromatography on flash silica gel, eluting with 15% ethyl acetate/hexane to give 6-bromomethyl-pyridine-2-carboxylic acid methyl ester (2.0 g, 20%) as a white solid. 1HNMR (CDCl3): δ 8.06 (d, J=8.0 Hz, 1H), 7.87 (dd, J=8.0 Hz, 1H), 7.70 (d, J=8.0 Hz, 1H), 4.65 (s, 2H), 4.02 (s, 3H). MS (APCI+): 231 (45), 235 (42).

後処理

  1. custom6-Bromomethyl-pyridine-2-carboxylic acid methyl ester was prepared
  2. temperaturewas heated
  3. temperatureat reflux overnight
  4. filtrationfiltered
  5. customevaporated
  6. custompurified by chromatography on flash silica gel
  7. washeluting with 15% ethyl acetate/hexane

出典と根拠

ORDレコード
ord-d9673c2fb2bc45969f422b986ec8dc57
出典データセット
uspto-grants-2010_11
特許番号
US07842825B2

関連ノート

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