Pyrazole → N-(3-nitro-5-(1H-pyrazol-1-yl)phenyl)acetamide

HRID 64120

反応式

HRID 64120 の反応式
Br[C:2]1[CH:3]=[C:4]([NH:11][C:12](=[O:14])[CH3:13])[CH:5]=[C:6]([N+:8]([O-:10])=[O:9])[CH:7]=1.[NH:15]1[CH:19]=[CH:18][CH:17]=[N:16]1.C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C=O)C.[Cu-]=O>[N+:8]([C:6]1[CH:5]=[C:4]([NH:11][C:12](=[O:14])[CH3:13])[CH:3]=[C:2]([N:15]2[CH:19]=[CH:18][CH:17]=[N:16]2)[CH:7]=1)([O-:10])=[O:9]

参加物

6

反応物 3

HCID 1048PyrazoleHCID 10796Cesium carbonateHCID 10658908N-(3-bromo-5-nitrophenyl)acetamide

生成物 1

HCID 117777661N-(3-nitro-5-(1H-pyrazol-1-yl)phenyl)acetamide収率 86%

試薬・触媒・溶媒 2

HCID 178419072HCID 178419072、化合物触媒HCID 6228Dimethylformamide溶媒

反応条件

温度
120 °C

実験手順

To a solution of N-(3-bromo-5-nitrophenyl)acetamide of Example 1(c) (10 g, 38.6 mmol) in DMF (100 ml) were added pyrazole (5.26 g, 77.2 mmol, 2.0 eq.), copper(I) oxide (1.104 g, 7.72 mmol, 0.2 eq.) and cesium carbonate (25.15 g, 77.2 mmol, 2.0 eq.) and the mixture was heated at 120° C. for 16 h. The mixture was quenched and extracted as in Example 1(d). The solvent was distilled off and the residue was purified by column chromatography over silica gel (30% ethyl acetate in hexane) to afford the compound in 86% yield (8.2 g). 1H NMR (300 MHz, DMSO-d6): δ 10.62 (s, 1H), 8.7 (d, 1H), 8.5-8.48 (m, 2H), 8.32 (t, 1H), 7.84 (d, 1H), 6.62 (t, 1H), 2.08 (s, 3H); LC-MS (ESI): Calculated mass: 246.22; Observed mass: 247.1 [M+H]+ (rt: 0.6 min).

後処理

  1. customThe mixture was quenched
  2. extractionextracted as in Example 1(d)
  3. distillationThe solvent was distilled off
  4. customthe residue was purified by column chromatography over silica gel (30% ethyl acetate in hexane)
  5. customto afford the compound in 86% yield (8.2 g)
  6. custom247.1 [M+H]+ (rt: 0.6 min)

出典と根拠

ORDレコード
ord-9ed3e0602a6e4738aa987771f44db444
出典データセット
uspto-grants-2016_09
特許番号
US09447091B2

関連ノート

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