Reaction equation
ClC(Cl)(O[C:5](=[O:11])OC(Cl)(Cl)Cl)Cl.[N:13]1[CH:18]=[CH:17][C:16]([C:19]2[C:28]3[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=3)[C:22]([NH2:29])=[CH:21][CH:20]=2)=[CH:15][CH:14]=1.C(N(CC)CC)C.[NH2:37][C:38]1[CH:39]=[C:40]2[C:44](=[CH:45][CH:46]=1)[NH:43][CH:42]=[C:41]2[CH:47]1[CH2:52][CH2:51][N:50]([CH3:53])[CH2:49][CH2:48]1.C(=O)([O-])[O-].[K+].[K+]>ClCCl>[CH3:53][N:50]1[CH2:51][CH2:52][CH:47]([C:41]2[C:40]3[C:44](=[CH:45][CH:46]=[C:38]([NH:37][C:5]([NH:29][C:22]4[C:23]5[C:28](=[CH:27][CH:26]=[CH:25][CH:24]=5)[C:19]([C:16]5[CH:15]=[CH:14][N:13]=[CH:18][CH:17]=5)=[CH:20][CH:21]=4)=[O:11])[CH:39]=3)[NH:43][CH:42]=2)[CH2:48][CH2:49]1Participants
7
Reactant 5
Product 1
Reagents, catalysts & solvents 1
Procedure
To a stirred solution of triphosgene (0.09 g, 0.31 mmole) in dichloromethane (15 ml) under argon, was added dropwise a solution of 4-(pyridin-4-yl)naphth-1-ylamine (D3, 0.17 g, 0.77 mmole) and triethylamine (0.12 ml, 0.83 mmole) in dichloromethane (10 ml). The mixture was then stirred at room temperature for 20 minutes, then a solution of 5-amino-3-(1-methylpiperidin-4-yl)-1H-indole (D2, 0.15 g, 0.66 mmole) in dichloromethane (10 ml) was slowly added. After stirring the mixture for 1 hour, dilute potassium carbonate solution (10 ml) was added. The precipitated solid mass was collected and purified by flash chromatography on silica gel eluting with CH2Cl2/MeOH/NH4OH (100:10:1) to afford the title compound as a buff powder (0.14 g).
Workup
- stirringAfter stirring the mixture for 1 hour
- customThe precipitated solid mass was collected
- custompurified by flash chromatography on silica gel eluting with CH2Cl2/MeOH/NH4OH (100:10:1)
Sources & evidence
- ORD record
- ord-238f452054944339b0db327ba733cb72
- Source dataset
- uspto-grants-2002_05
- Patent number
- US06391891B1
Linked notes
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