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

HRID 348413

反応式

[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]

参加物

反応条件

温度: 80 °C

実験手順

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.

後処理

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

出典と根拠

ORDレコード: ord-e77d4e7f081842e0af2eed0630b013d8
出典データセット: uspto-grants-2007_02
DOI: 10.6084/m9.figshare.5104873.v1
特許番号: US07176311B2

反応式

参加物

反応物 3

生成物 1

試薬・触媒・溶媒 1

反応条件

実験手順

後処理

出典と根拠

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