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

HRID 631924

反応式

HRID 631924 の反応式
[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]

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 241Benzene溶媒

反応条件

温度
90 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-f95408ea2543478298e25abe0fb6cd58
出典データセット
uspto-grants-2016_04
特許番号
US09321738B2

関連ノート

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