Trimethylsilylacetylene → 2,3-Dimethoxy-5-[2-(trimethylsilyl)ethynyl]pyridine

HRID 709046노트

반응식

HRID 709046 반응식
Br[C:2]1[CH:3]=[C:4]([O:10][CH3:11])[C:5]([O:8][CH3:9])=[N:6][CH:7]=1.[C:12]([Si:14]([CH3:17])([CH3:16])[CH3:15])#[CH:13]>[Cu]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.C(N(CC)CC)C>[CH3:9][O:8][C:5]1[C:4]([O:10][CH3:11])=[CH:3][C:2]([C:13]#[C:12][Si:14]([CH3:17])([CH3:16])[CH3:15])=[CH:7][N:6]=1

참가 물질

6

반응물 2

HCID 66111TrimethylsilylacetyleneHCID 125630845-Bromo-2,3-dimethoxypyridine

생성물 1

HCID 467378382,3-Dimethoxy-5-[2-(trimethylsilyl)ethynyl]pyridine수율 71%

시약·촉매·용매 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)촉매HCID 178418476HCID 178418476, 화합물촉매HCID 8471Triethylamine용매

실험 절차

Copper (I) iodide (0.56 g, 2.9 mmol), bis(triphenylphosphine)palladium(II) dichloride (2.1 g, 2.9 mmol), and 5-bromo-2,3-dimethoxypyridine (12.8 g, 59 mmol) were added to triethylamine (80 ml) which produced a yellow suspension. The reaction was thoroughly degassed and ethynyltrimethylsilane (5.8 g, 59 mmol) was added to the stirred suspension which was then stirred for 16 hours and concentrated. The crude material was purified by column chromatography (SiO2; 0-10% ethyl acetate in petrol) to afford 2,3-dimethoxy-5-[(trimethylsilyl)ethynyl]pyridine (9.8 g, 71%).

후처리

  1. customproduced a yellow suspension
  2. customThe reaction was thoroughly degassed
  3. concentrationconcentrated
  4. customThe crude material was purified by column chromatography (SiO2; 0-10% ethyl acetate in petrol)

출처 및 근거

ORD 기록
ord-d057327a4502493bb3831f6eb56adfea
출처 데이터셋
uspto-grants-2015_11
특허 번호
US09180122B2

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