3-Ethynylpyridine → 3-[2-(4,4,5,5-Tetramethyl-[1,3,2]dioxaborolan-2-YL)-vinyl]-pyridine

HRID 1868342노트

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HRID 1868342 반응식
[C:1]([C:3]1[CH:4]=[N:5][CH:6]=[CH:7][CH:8]=1)#[CH:2].[CH3:9][C:10]1([CH3:17])[C:14]([CH3:16])([CH3:15])[O:13][BH:12][O:11]1>C1(C)C=CC=CC=1>[CH3:9][C:10]1([CH3:17])[C:14]([CH3:16])([CH3:15])[O:13][B:12]([CH:2]=[CH:1][C:3]2[CH:4]=[N:5][CH:6]=[CH:7][CH:8]=2)[O:11]1

참가 물질

4

반응물 2

HCID 1860033-EthynylpyridineHCID 27347684,4,5,5-Tetramethyl[1,3,2]dioxaborolane

생성물 1

HCID 667342383-[2-(4,4,5,5-Tetramethyl-[1,3,2]dioxaborolan-2-YL)-vinyl]-pyridine

시약·촉매·용매 1

HCID 1140Toluene용매

반응 조건

온도
50 °C

실험 절차

Commercially available 3-ethynyl-pyridine 3b (1.03 g, 10 mmol) and 4,4,5,5-tetramethyl-[1,3,2]dioxaborolane (7.26 mL, 50 mmole) in toluene (40 mL) were combined with carbonylchlorohydridotris(triphenylphosphine) ruthenium (II), RuHCl(CO)(PPh3) (476 mg, 0.50 mmol) at ambient temperature and the reaction mixture was heated at 50° C. in an oil-bath for 16 h. The toluene was evaporated and the crude compound was diluted with ethyl acetate and washed with saturated sodium bicarbonate solution, saturated sodium chloride solution, and water. The organic extracts were dried over MgSO4, filtered, and evaporated in vacuo. The crude product was eluted with a gradient of 10:1 to 2:1 hexane/ethyl acetate by flash chromatography to yield 3-[2-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-vinyl]-pyridine Compound 3c (2.2 g, 95% yield) as a yellow syrup. 1H NMR (300 MHz, CDCl3) δ 8.75 (d, 1H), 8.54 (dd, 1H), 7.83 (dt, 1H), 7.39 (d, 1H), 7.31 (dd, 1H), 6.27 (d, 1H), 1.34 (s, 12H); MS (ESI) m/z: 232.14 (M+H+).

후처리

  1. customThe toluene was evaporated
  2. additionthe crude compound was diluted with ethyl acetate
  3. washwashed with saturated sodium bicarbonate solution, saturated sodium chloride solution, and water
  4. dry with materialThe organic extracts were dried over MgSO4
  5. filtrationfiltered
  6. customevaporated in vacuo
  7. washThe crude product was eluted with a gradient of 10:1 to 2:1 hexane/ethyl acetate by flash chromatography

출처 및 근거

ORD 기록
ord-0033b6c0f3424604884f7ad01b879016
출처 데이터셋
uspto-grants-2009_12
특허 번호
US07635703B2

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