Triethylamine → 5-Methyl-2-(2-(trimethylsilyl)ethynyl)pyridine

HRID 2175418ノート

反応式

HRID 2175418 の反応式
Br[C:2]1[CH:7]=[CH:6][C:5]([CH3:8])=[CH:4][N:3]=1.[C:9]([Si:11]([CH3:14])([CH3:13])[CH3:12])#[CH:10].C(N(CC)CC)C>[Cu](I)I.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[CH3:8][C:5]1[CH:6]=[CH:7][C:2]([C:10]#[C:9][Si:11]([CH3:14])([CH3:13])[CH3:12])=[N:3][CH:4]=1

参加物

6

反応物 3

HCID 8471TriethylamineHCID 66111TrimethylsilylacetyleneHCID 5642162-Bromo-5-methylpyridine

生成物 1

HCID 447549315-Methyl-2-(2-(trimethylsilyl)ethynyl)pyridine収率 76%

試薬・触媒・溶媒 2

HCID 83717Copper iodide触媒HCID 178418476HCID 178418476、化合物触媒

反応条件

温度
25 °C

実験手順

The mixture of 2-bromo-5-methylpyridine (5.0 g, 29.1 mmol), ethynyltrimethylsilane (3.42 g, 34.88 mmol), Copper iodide (0.61 g, 332 mg) and Pd(PPh3)2Cl2 (0.61 g, 0.871 mmol) was dissolved in triethylamine (6.4 mL, 261 mmol). The solution was purged with N2 3 times. The solution was stirred for overnight under 25° C. The solvent was removed under reduced pressure. The residue was separated by silca gel chromatography with the eluent of PE/EA=20/1. The product was obtained as a yellow solid (4.15 g, 76%). 1H NMR (400 MHz, CDCl3) δ 8.41 (s, 1H), 7.46 (dd, J=7.9, 1.5 Hz, 1H), 7.36 (d, J=7.9 Hz, 1H), 2.35 (s, 3H), 0.28 (s, 9H); LRMS (ES) calculated M+H for C11H16NSi: 190.3. Found: 190.2.

後処理

  1. customThe solution was purged with N2 3 times
  2. customThe solvent was removed under reduced pressure
  3. customThe residue was separated by silca gel chromatography with the eluent of PE/EA=20/1

出典と根拠

ORDレコード
ord-51860b5220224f50878726ba5d29a3f0
出典データセット
uspto-grants-2015_06
特許番号
US09062059B2

反応ノート

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