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

HRID 1453819

反応式

HRID 1453819 の反応式
[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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-e12048c5340045739f9865604b71113a
出典データセット
uspto-grants-2009_01
特許番号
US07476666B2

関連ノート

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