Cesium carbonate → 2-(2-{[tert-Butyl(dimethyl)silyl]oxy}ethyl)-3-ethyl-4-nitropyrazole-5-carboxamide

HRID 348413

반응식

HRID 348413 반응식
[CH2:1]([C:3]1[C:7]([N+:8]([O-:10])=[O:9])=[C:6]([C:11]([NH2:13])=[O:12])[NH:5][N:4]=1)[CH3:2].C(=O)([O-])[O-].[Cs+].[Cs+].Br[CH2:21][CH2:22][O:23][Si:24]([C:27]([CH3:30])([CH3:29])[CH3:28])([CH3:26])[CH3:25]>C(#N)C>[Si:24]([O:23][CH2:22][CH2:21][N:4]1[C:3]([CH2:1][CH3:2])=[C:7]([N+:8]([O-:10])=[O:9])[C:6]([C:11]([NH2:13])=[O:12])=[N:5]1)([C:27]([CH3:30])([CH3:29])[CH3:28])([CH3:26])[CH3:25]

참가 물질

5

반응물 3

HCID 10796Cesium carbonateHCID 3608067(2-Bromoethoxy)-tert-butyldimethylsilaneHCID 178438045HCID 178438045, 화합물

생성물 1

HCID 600611012-(2-{[tert-Butyl(dimethyl)silyl]oxy}ethyl)-3-ethyl-4-nitropyrazole-5-carboxamide

시약·촉매·용매 1

HCID 6342Acetonitrile용매

반응 조건

온도
80 °C

실험 절차

A mixture of 3-ethyl-4-nitro-1H-pyrazole-5-carboxamide (WO, 9849166), (4.9 g, 26.6 mmol), cesium carbonate (21.0 g, 64.5 mmol) and (2-bromoethoxy)-tert-butyldimethylsilane (7.0 g, 29.0 mmol) in acetonitrile (400 ml) was stirred at 80° C. for 20 hours. The cooled mixture was concentrated under reduced pressure and the residue was partitioned between ethyl acetate (200 ml) and water (100 ml). The layers were separated, the organic phase washed with water (3×50 ml), dried (Na2SO4) and evaporated under reduced pressure. The crude product was purified by column chromatography on silica gel, using ethyl acetate as eluant, and repeated using an elution gradient of pentane:ethyl acetate (50:50 to 0:100), to give some of the desired compound.

후처리

  1. concentrationThe cooled mixture was concentrated under reduced pressure
  2. customthe residue was partitioned between ethyl acetate (200 ml) and water (100 ml)
  3. customThe layers were separated
  4. washthe organic phase washed with water (3×50 ml)
  5. dry with materialdried (Na2SO4)
  6. customevaporated under reduced pressure
  7. customThe crude product was purified by column chromatography on silica gel

출처 및 근거

ORD 기록
ord-e77d4e7f081842e0af2eed0630b013d8
출처 데이터셋
uspto-grants-2007_02
특허 번호
US07176311B2

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