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

HRID 64120

반응식

HRID 64120 반응식
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]

참가 물질

6

반응물 3

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

생성물 1

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

시약·촉매·용매 2

HCID 178419072HCID 178419072, 화합물촉매HCID 6228Dimethylformamide용매

반응 조건

온도
120 °C

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-9ed3e0602a6e4738aa987771f44db444
출처 데이터셋
uspto-grants-2016_09
특허 번호
US09447091B2

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