Acrylonitrile → 4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole-1-propanenitrile

HRID 240778

반응식

HRID 240778 반응식
[CH3:1][C:2]1([CH3:14])[C:6]([CH3:8])([CH3:7])[O:5][B:4]([C:9]2[CH:10]=[N:11][NH:12][CH:13]=2)[O:3]1.[C:15](#[N:18])[CH:16]=[CH2:17].N12CCCN=C1CCCCC2>C(#N)C>[CH3:1][C:2]1([CH3:14])[C:6]([CH3:7])([CH3:8])[O:5][B:4]([C:9]2[CH:13]=[N:12][N:11]([CH2:17][CH2:16][C:15]#[N:18])[CH:10]=2)[O:3]1

참가 물질

5

반응물 3

HCID 7855AcrylonitrileHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 27740104-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole

생성물 1

HCID 569657334-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole-1-propanenitrile

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

To a solution of 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (5.00 g, 25.8 mmol) in acetonitrile (50 mL) was added acrylonitrile (3.4 mL, 52 mmol) followed by 1,8-diazabicyclo[5.4.0]undec-7-ene (1.94 mL, 12.9 mmol). After about 2 hours, the reaction mixture was concentrated under reduced pressure. The crude material was then dissolved in a minimal amount of dichloromethane and purified via silica gel chromatography eluting with a gradient of 10-50% ethyl acetate in heptane to afford the title compound. 1H NMR (400 MHz, DMSO-d6) δ ppm 8.03 (s, 1H), 7.64 (s, 1H), 4.40 (t, J=6.4 Hz, 2H), 3.06 (t, J=6.4 Hz, 2H), 1.26 (s, 12H). MS (ESI+) m/z 247.3 (M+H)+.

후처리

  1. concentrationthe reaction mixture was concentrated under reduced pressure
  2. dissolutionThe crude material was then dissolved in a minimal amount of dichloromethane
  3. custompurified via silica gel chromatography
  4. washeluting with a gradient of 10-50% ethyl acetate in heptane

출처 및 근거

ORD 기록
ord-b2d2801954ce49ed8fc6b028a34679cf
출처 데이터셋
uspto-grants-2014_02
특허 번호
US08648069B2

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