反应 #1244271

ord-9b99331a26a94464b68b74bc370e9dda

反应方程式

C#CCNC(=O)CBr
alkyne
C#CCNC(=O)CBr
2-Bromo-N-(prop-2-ynyl)acetamide
C#CCn1ccnc1[N+](=O)[O-]
2-nitroimidazole
C#CCn1ccnc1[N+](=O)[O-]
2-Nitro-1-(prop-2-ynyl)-1H-imidazole
O=C([O-])[O-].[K+].[K+]
K2CO3
C#CCNC(=O)Cn1ccnc1[N+](=O)[O-]
white solid
收率 18.0%
C#CCNC(=O)Cn1ccnc1[N+](=O)[O-]
2-(2-Nitro-1H-imidazol-1-yl)-N-(prop-2-ynyl)acetamide
收率 18.0%

溶剂

反应条件

详细条件
See reaction.notes.procedure_details.

后处理

  1. 1
    过滤the resultant precipitate (1.2 g) was filtered off
  2. 2
    洗涤washed with water (2×40 mL)
  3. 3
    萃取The aqueous layer was extracted into EtOAc
  4. 4
    浓缩The organic layer was concentrated to dryness
  5. 5
    其他The material was purified on a silica gel cartridge

实验过程

To a round bottom flask was added alkyne 18 (1.56 g, 8.84 mmol), 2-nitroimidazole 10 (1 g, 8.84 mmol) and K2CO3 (1.22 g, 8.84 mmol) in DMF (10 mL). The reaction was stirred overnight. The reaction was diluted with water (100 mL) and the resultant precipitate (1.2 g) was filtered off and washed with water (2×40 mL). The aqueous layer was extracted into EtOAc. The organic layer was concentrated to dryness and combined with the precipitate. The material was purified on a silica gel cartridge using EtOAc:Hex as the eluent to afford a 19 white solid (324 mg, 18%). Mass Spec (lo-res): Calc'd for C8H8N4O3: 208.06; found: 209.10 (M+H).

来源

DOI: 10.6084/m9.figshare.5104873.v1专利: US07807394B2uspto-grants-2010_10