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

HRID 386047

반응식

HRID 386047 반응식
[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

참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 1140Toluene용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-b1b63a839673446cbd034ed3685dcd55
출처 데이터셋
uspto-grants-2013_02
특허 번호
US08367706B2

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