Cesium carbonate → Dimethyl 4-benzyloxy-1-[cyano(phenyl)methyl]-1H-pyrazole-3,5-dicarboxylate

HRID 1453825

반응식

HRID 1453825 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[CH:23]([C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)[C:24]#[N:25].C([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]([CH:23]([C:24]#[N:25])[C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[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 22044Bromobenzyl CyanideHCID 57528491dimethyl 4-benzyloxy-1H-pyrazole-3,5-dicarboxylate

생성물 1

HCID 68953781Dimethyl 4-benzyloxy-1-[cyano(phenyl)methyl]-1H-pyrazole-3,5-dicarboxylate

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

A solution of dimethyl 4-benzyloxy-1H-pyrazole-3,5-dicarboxylate (1.0 g, 3.45 mmol) and bromo(phenyl)acetonitrile (810 mg, 4.13 mmol) in anhydrous DMF was treated with Cs2CO3 (1.46 g, 4.48 mmol) and stirred at room temperature for 3 days. The solvent was removed in vacuo and the residue was partitioned between EtOAc and water. The aqueous layer was extracted with EtOAc several times, and the combined organic layers were dried over Na2SO4 and concentrated in vacuo. The resulting residue was purified by flash column chromatography on silica gel using a gradient elution of 0-20% EtOAc/hexanes. Collection and concentration of the appropriate fractions yielded the title product as a yellow oil. 1H NMR (400 MHz, d6-DMSO) δ 7.70 (s, 1H), 7.50-7.45 (m, 3H), 7.43-7.29 (m, 7H), 5.08 (s, 2H), 3.86 (s, 3H), 3.81 (s, 3H); ES MS (M+1)=406.

후처리

  1. customThe solvent was removed in vacuo
  2. customthe residue was partitioned between EtOAc and water
  3. extractionThe aqueous layer was extracted with EtOAc several times
  4. dry with materialthe combined organic layers were dried over Na2SO4
  5. concentrationconcentrated in vacuo
  6. customThe resulting residue was purified by flash column chromatography on silica gel using
  7. washa gradient elution of 0-20% EtOAc/hexanes
  8. customCollection and concentration of the appropriate fractions

출처 및 근거

ORD 기록
ord-051401307b164482b4af2cae00ad380f
출처 데이터셋
uspto-grants-2009_01
특허 번호
US07476666B2

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