Trimethylsilylmethyl Azide → 5-(4-bromo-2-fluoro-phenyl)-3-trimethylsilanylmethyl-3H-[1,2,3]triazole-4-carboxylic acid ethyl ester

HRID 631924

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HRID 631924 반응식
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]#[C:9][C:10]([O:12][CH2:13][CH3:14])=[O:11])=[C:4]([F:15])[CH:3]=1.[N:16]([CH2:19][Si:20]([CH3:23])([CH3:22])[CH3:21])=[N+:17]=[N-:18]>C1C=CC=CC=1>[CH2:13]([O:12][C:10]([C:9]1[N:16]([CH2:19][Si:20]([CH3:23])([CH3:22])[CH3:21])[N:17]=[N:18][C:8]=1[C:5]1[CH:6]=[CH:7][C:2]([Br:1])=[CH:3][C:4]=1[F:15])=[O:11])[CH3:14]

참가 물질

4

반응물 2

HCID 150751Trimethylsilylmethyl AzideHCID 119085651Ethyl 3-(4-bromo-2-fluorophenyl)prop-2-ynoate

생성물 1

HCID 1317354315-(4-bromo-2-fluoro-phenyl)-3-trimethylsilanylmethyl-3H-[1,2,3]triazole-4-carboxylic acid ethyl ester

시약·촉매·용매 1

HCID 241Benzene용매

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온도
90 °C

실험 절차

In a 50 mL pear-shaped flask, ethyl 3-(4-bromo-2-fluorophenyl)propiolate (1.27 g, 4.68 mmol) and (azidomethyl)trimethylsilane (2.42 g, 2.78 mL, 18.7 mmol, Eq: 4) were combined with benzene (3.5 mL) to give a light yellow solution. The reaction mixture was heated to 90° C. and stirred for 4 h. The reaction mixture was concentrated in vacuo. The crude material was purified by flash chromatography (silica gel, 80 g, 0% to 20% EtOAc in heptane) to afford 616 mg (33%) of the desired less polar regio-isomer as a white solid. (M+H)+=400.0/402.0 m/e.

후처리

  1. customto give a light yellow solution
  2. concentrationThe reaction mixture was concentrated in vacuo
  3. customThe crude material was purified by flash chromatography (silica gel, 80 g, 0% to 20% EtOAc in heptane)
  4. customto afford 616 mg (33%) of the

출처 및 근거

ORD 기록
ord-f95408ea2543478298e25abe0fb6cd58
출처 데이터셋
uspto-grants-2016_04
특허 번호
US09321738B2

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