Cesium carbonate → Dimethyl 4-benzyloxy-1-(2-bromoethyl)-1H-pyrazole-3,5-dicarboxylate

HRID 1453819

반응식

HRID 1453819 반응식
[CH2:1]([O:8][C:9]1[C:10]([C:18]([O:20][CH3:21])=[O:19])=[N:11][NH:12][C:13]=1[C:14]([O:16][CH3:17])=[O:15])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([O-])([O-])=O.[Cs+].[Cs+].[Br:28][CH:29](Br)[CH3:30]>CN(C=O)C>[CH2:1]([O:8][C:9]1[C:13]([C:14]([O:16][CH3:17])=[O:15])=[N:12][N:11]([CH2:30][CH2:29][Br:28])[C:10]=1[C:18]([O:20][CH3:21])=[O:19])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

참가 물질

5

반응물 3

HCID 10796Cesium carbonateHCID 112011,1-DibromoethaneHCID 57528491dimethyl 4-benzyloxy-1H-pyrazole-3,5-dicarboxylate

생성물 1

HCID 57528492Dimethyl 4-benzyloxy-1-(2-bromoethyl)-1H-pyrazole-3,5-dicarboxylate

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

To a solution of dimethyl 4-benzyloxy-1H-pyrazole-3,5-dicarboxylate (1.0 g, 3.45 mmol) in anhydrous DMF (20 mL) were added Cs2CO3 (1.35 g, 4.13 mmol) and dibromoethane (2.27 g, 12.1 mmol). The reaction mixture was stirred at room temperature for 2 hours and then filtered. The filtrate was concentrated in vacuo and the residue was purified by flash chromatography on silica gel using a 0-25% EtOAc/hexanes gradient elution. Collection and concentration of the appropriate fractions provided the title compound as a white solid. 1H NMR (400 MHz, d6-DMSO) δ 7.45-7.34 (m, 5H), 5.06 (s, 2H), 4.88 (t, J=6.4 Hz, 2H), 3.86-3.79 (m, 8H).

후처리

  1. filtrationfiltered
  2. concentrationThe filtrate was concentrated in vacuo
  3. customthe residue was purified by flash chromatography on silica gel using
  4. washa 0-25% EtOAc/hexanes gradient elution
  5. customCollection and concentration of the appropriate fractions

출처 및 근거

ORD 기록
ord-e12048c5340045739f9865604b71113a
출처 데이터셋
uspto-grants-2009_01
특허 번호
US07476666B2

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