4,7-dimethyl-2,3-dihydro-1H-indole-2,3-dione → 3-(4-Fluoro-benzyl)-5,8-dimethyl-9H-1,2,3a,4,9,10-hexaaza-cyclopenta[b]fluorene
Reaction equation
[CH3:1][C:2]1[CH:10]=[CH:9][C:8]([CH3:11])=[C:7]2[C:3]=1[C:4](=O)[C:5](=O)[NH:6]2.[F:14][C:15]1[CH:28]=[CH:27][C:18]([CH2:19][C:20]2[N:21]([NH2:26])[C:22]([NH2:25])=[N:23][N:24]=2)=[CH:17][CH:16]=1>C(O)CO.O>[F:14][C:15]1[CH:28]=[CH:27][C:18]([CH2:19][C:20]2[N:21]3[C:22]([N:25]=[C:5]4[C:4](=[N:26]3)[C:3]3[C:7](=[C:8]([CH3:11])[CH:9]=[CH:10][C:2]=3[CH3:1])[NH:6]4)=[N:23][N:24]=2)=[CH:17][CH:16]=1Participants
5
Reactant 2
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 125 °C
Procedure
According to the general cyclization procedure (for Example 27), 0.60 mmol of 4,7-dimethyl-1H-indole-2,3-dione (105 mg) and 0.70 mmol of (4-fluoro-benzyl)-[1,2,4]triazole-3,4-diamine (145 mg) in 2 mL of ethylene glycol was stirred at 125° C. overnight (18 hr). The mixture was cooled to room temperature, diluted with water (10 mL), stirred for 15 min. The precipitated product was collected by filtration, washed with MeOH+water 1:1. Dried on high vacuum. The crude product (187 mg) was suspended in anhydrous ethanol (6 mL), heated to reflux, sonicated while hot, allowed to cool overnight, filtered, washed with ice-cold methanol, filtered and dried on high vacuum.
Workup
- temperatureThe mixture was cooled to room temperature
- stirringstirred for 15 min
- filtrationThe precipitated product was collected by filtration
- washwashed with MeOH+water 1:1
- customDried on high vacuum
- temperatureheated
- temperatureto reflux
- customsonicated while hot,
- temperatureto cool overnight
- filtrationfiltered
- washwashed with ice-cold methanol
- filtrationfiltered
- customdried on high vacuum
Sources & evidence
- ORD record
- ord-79e6422ddd6943a281b9842203536ba5
- Source dataset
- uspto-grants-2006_05
- Patent number
- US07037909B2
Reaction notes
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