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

HRID 2176087노트

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HRID 2176087 반응식
[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

참가 물질

6

반응물 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

생성물 1

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

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

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)+.

후처리

  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)

출처 및 근거

ORD 기록
ord-364b3651b86448148781e30cfb4b8f42
출처 데이터셋
uspto-grants-2015_06
특허 번호
US09063126B2

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