Methyl propiolate → Methyl 1-[(6-bromopyridin-2-yl)methyl]-1H-1,2,3-triazole-5-carboxylate

HRID 386047

反応式

HRID 386047 の反応式
[N:1]([CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([Br:11])[N:6]=1)=[N+:2]=[N-:3].[C:12]([O:16][CH3:17])(=[O:15])[C:13]#[CH:14]>C1(C)C=CC=CC=1>[Br:11][C:7]1[N:6]=[C:5]([CH2:4][N:1]2[C:13]([C:12]([O:16][CH3:17])=[O:15])=[CH:14][N:3]=[N:2]2)[CH:10]=[CH:9][CH:8]=1

参加物

4

反応物 2

HCID 13536Methyl propiolateHCID 453574032-(Azidomethyl)-6-bromopyridine

生成物 1

HCID 59525904Methyl 1-[(6-bromopyridin-2-yl)methyl]-1H-1,2,3-triazole-5-carboxylate

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

実験手順

2-(Azidomethyl)-6-bromopyridine (Example 470 Step 1) (600 mg, 2.82 mmol) and methyl propiolate (355 μL, 4.22 mmol) were combined in toluene (10 mL) and stirred at reflux overnight. The solvent was evaporated, and the residue was purified by flash chromatography (20-100% EtOAc/hexanes), whereby good separation of the two regioisomeric products was achieved. TLC, LC/MS, and 1H NMR analysis confirmed that the first spot (less polar, higher Rf) corresponded to the desired regioisomer. The title compound was isolated as a colorless oil.

後処理

  1. temperatureat reflux overnight
  2. customThe solvent was evaporated
  3. customthe residue was purified by flash chromatography (20-100% EtOAc/hexanes), whereby good separation of the two regioisomeric products

出典と根拠

ORDレコード
ord-b1b63a839673446cbd034ed3685dcd55
出典データセット
uspto-grants-2013_02
特許番号
US08367706B2

関連ノート

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