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

HRID 2175418노트

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HRID 2175418 반응식
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

참가 물질

6

반응물 3

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

생성물 1

HCID 447549315-Methyl-2-(2-(trimethylsilyl)ethynyl)pyridine수율 76%

시약·촉매·용매 2

HCID 83717Copper iodide촉매HCID 178418476HCID 178418476, 화합물촉매

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온도
25 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-51860b5220224f50878726ba5d29a3f0
출처 데이터셋
uspto-grants-2015_06
특허 번호
US09062059B2

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