Water → 5-(2-Bromovinyl)-2-methylpyridine

HRID 2176087ノート

反応式

HRID 2176087 の反応式
[CH3:1][C:2]1[CH:7]=[CH:6][C:5](/[CH:8]=[CH:9]/B2OC(C)(C)C(C)(C)O2)=[CH:4][N:3]=1.[Br:19]N1C(=O)CCC1=O.C(N(CC)CC)C.O>C(#N)C>[Br:19][CH:9]=[CH:8][C:5]1[CH:6]=[CH:7][C:2]([CH3:1])=[N:3][CH:4]=1

参加物

6

反応物 4

HCID 962WaterHCID 8471TriethylamineHCID 67184N-bromobutanimideHCID 57416208(e)-2-Methyl-5-(2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)vinyl)pyridine

生成物 1

HCID 722566695-(2-Bromovinyl)-2-methylpyridine

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

実験手順

A solution of (E)-2-methyl-5-(2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)vinyl)-pyridine (1.0 g, 4.08 mmol; Example 23B) in acetonitrile (10 mL) was treated with N-bromosuccinimide (0.346 mL, 4.08 mmol; Aldrich) and triethylamine (0.625 mL, 4.49 mmol; Aldrich) and stirred at room temperature for 16 hours. Water was added and the mixture was extracted several times with ethyl acetate. The combined organic extracts were concentrated, and the resulting material was purified by flash chromatography (silica gel, hexane/ethyl acetate, 3:1) to afford the title compound as a 1.2:1 Z/E mixture: 1H NMR (300 MHz, CDCl3) δ ppm 2.54 (s, 3H), 2.57 (s, 3.6H), 6.52 (d, J=14 Hz, 1.2H), 6.75-6.85 (d, J=14 Hz, 1H), 7.01-7.22 (m, 4.4H), 7.52 (dd, J=8, 2 Hz, 1H), 8.07 (dd, J=8, 2 Hz, 1.2H), 8.43 (d, J=2 Hz, 1H), 8.66 (d, J=2 Hz, 1.2H); MS (DCI/NH3) m/z 198/200 (M+H)+.

後処理

  1. extractionthe mixture was extracted several times with ethyl acetate
  2. concentrationThe combined organic extracts were concentrated
  3. customthe resulting material was purified by flash chromatography (silica gel, hexane/ethyl acetate, 3:1)

出典と根拠

ORDレコード
ord-364b3651b86448148781e30cfb4b8f42
出典データセット
uspto-grants-2015_06
特許番号
US09063126B2

反応ノート

読み込み中…