Cesium fluoride → 2-(Bromomethyl)-6-(2,5-dimethyl-1H-pyrrol-1-yl)-4-methylpyridine

HRID 73481

反応式

HRID 73481 の反応式
[CH3:1][C:2]1[N:3]([C:8]2[CH:13]=[C:12]([CH3:14])[CH:11]=[C:10]([CH2:15][Si](C)(C)C)[N:9]=2)[C:4]([CH3:7])=[CH:5][CH:6]=1.[Br:20]C(F)(F)C(F)(F)Br.[F-].[Cs+]>CN(C=O)C>[Br:20][CH2:15][C:10]1[CH:11]=[C:12]([CH3:14])[CH:13]=[C:8]([N:3]2[C:2]([CH3:1])=[CH:6][CH:5]=[C:4]2[CH3:7])[N:9]=1

参加物

5

反応物 3

HCID 25953Cesium fluorideHCID 313011,2-Dibromo-1,1,2,2-tetrafluoroethaneHCID 426256202-(2,5-Dimethyl-1H-pyrrol-1-yl)-4-methyl-6-((trimethylsilyl)methyl)pyridine

生成物 1

HCID 445431562-(Bromomethyl)-6-(2,5-dimethyl-1H-pyrrol-1-yl)-4-methylpyridine収率 99%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

To a solution of 9 (5.6 g, 21 mmol) in DMF (100 mL) was added 1,2-dibromotetrafluoroethane (10 g, 42 mmol) and CsF (6.4 g, 42 mmol). The reaction was allowed to stir at room temperature for 3 h, and the resulting purple solution was concentrated and loaded directly on flash column chromatography (EtOAc/hexanes, 1:19-1:9) to give 6 (5.7 g, 20.8 mmol, 99%) as a pale yellow oil: 1H NMR (500 MHz, CDCl3) δ 2.19 (s, 6H), 2.47 (s, 3H), 4.56 (s, 2H), 5.93 (s, 2H), 7.01 (s, 1H), 7.30 (s, 1H); 13C NMR (125 MHz, CDCl3) δ 13.3, 21.1, 33.5, 107.1, 121.8, 122.9, 128.5, 150.7, 151.7, 156.3; LCQ-MS (M+H+) calcd for C13H16BrN2 279. found 279; LC-TOF-MS (M+H+) calcd for C13H16BrN2 279.04969. found 279.04963.

後処理

  1. concentrationthe resulting purple solution was concentrated

出典と根拠

ORDレコード
ord-8b7411f71962440c8a48ded0043556e4
出典データセット
uspto-grants-2014_09
特許番号
US08829187B1

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