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

HRID 1453865

반응식

HRID 1453865 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.Br[C:23]([Br:26])([CH3:25])C.[C:27]([O-])([O-])=O.[Cs+].[Cs+]>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]([CH2:27][CH2:25][CH2:23][Br:26])[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 116582,2-DibromopropaneHCID 57528491dimethyl 4-benzyloxy-1H-pyrazole-3,5-dicarboxylate

생성물 1

HCID 69080907Dimethyl 4-benzyloxy-1-(3-bromopropyl)-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 (200 mg, 0.689 mmol) in DMF (3 mL) under an atmosphere of nitrogen at 0° C. was added dibromopropane (211 μL, 2.067 mmol) and Cs2CO3 (269 mg, 0.827 mmol). The ice bath was removed, and the reaction was stirred at room temperature overnight. The solvent was removed in vacuo, and the resulting residue was partitioned between EtOAc and water. The aqueous layer was extracted into EtOAc once, and the combined organic extracts were washed with brine, dried over Na2SO4, and concentrated in vacuo. the residue was purified by flash column chromatography on silica gel using a 0-50% EtOAc/hexanes gradient elution. Collection and concentration of the appropriate fractions afforded the compound. 1H NMR (400 MHz, CDCl3) δ 7.47-7.44 (m, 2H), 7.40-7.34 (m, 3M), 5.13 (s, 2H), 4.71-4.67 (t, 2H), 3.96 (s, 3H), 3.87 (s, 3H), 3.39-3.36 (t, 2H), 2.45-2.38 (dt, 2H); ES MS (M+1)=412.

후처리

  1. customThe ice bath was removed
  2. customThe solvent was removed in vacuo
  3. customthe resulting residue was partitioned between EtOAc and water
  4. extractionThe aqueous layer was extracted into EtOAc once
  5. washthe combined organic extracts were washed with brine
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated in vacuo
  8. customthe residue was purified by flash column chromatography on silica gel using
  9. washa 0-50% EtOAc/hexanes gradient elution
  10. customCollection and concentration of the appropriate fractions
  11. customafforded the compound

출처 및 근거

ORD 기록
ord-23e4a8f716d14da49f8053f2daa917f6
출처 데이터셋
uspto-grants-2009_01
특허 번호
US07476666B2

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