Cesium carbonate → 4-Chloro-5-(3-chloropropoxy)-7-[1-(tert-butoxycarbonyl)-5-(piperidin-1-ylmethyl)indol-2-yl]isoindolinone
Reaction equation
[Cl:1][C:2]1[C:10]([OH:11])=[CH:9][C:8]([C:12]2[N:13]([C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30])[C:14]3[C:19]([C:20]=2C)=[CH:18][C:17]([CH2:22][N:23]2[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]2)=[CH:16][CH:15]=3)=[C:7]2[C:3]=1[CH2:4][NH:5][C:6]2=[O:36].C(=O)([O-])[O-].[Cs+].[Cs+].[Cl:43][CH2:44][CH2:45][CH2:46]I>C(#N)C>[Cl:1][C:2]1[C:10]([O:11][CH2:46][CH2:45][CH2:44][Cl:43])=[CH:9][C:8]([C:12]2[N:13]([C:29]([O:31][C:32]([CH3:34])([CH3:33])[CH3:35])=[O:30])[C:14]3[C:19]([CH:20]=2)=[CH:18][C:17]([CH2:22][N:23]2[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]2)=[CH:16][CH:15]=3)=[C:7]2[C:3]=1[CH2:4][NH:5][C:6]2=[O:36]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
In a similar manner to Step 1 of Example 433, 4-chloro-5-hydroxy-7-[1-(tert-butoxycarbonyl)-5-(piperidin-1-ylmethyl)methylindol-2-yl]isoindolinone (100 mg, 0.202 mmol) was suspended in acetonitrile (5.0 mL), and the suspension was treated with cesium carbonate (98.7 mg, 0.303 mmol) and 1-chloro-3-iodopropane (0.026 mL, 0.242 mmol), followed by purification by flash column chromatography (chloroform/methanol=19/1, 4/1) to obtain 4-chloro-5-(3-chloropropoxy)-7-[1-(tert-butoxycarbonyl)-5-(piperidin-1-ylmethyl)indol-2-yl]isoindolinone (97.7 mg, yield 84%).
Workup
- customfollowed by purification by flash column chromatography (chloroform/methanol=19/1, 4/1)
Sources & evidence
- ORD record
- ord-934a2d9f73474745bfc5b298c065623f
- Source dataset
- uspto-grants-2010_06
- Patent number
- US07745641B2
Reaction notes
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