Reaction equation
[Cl:1][C:2]1[C:10](OS(C(F)(F)F)(=O)=O)=[CH:9][C:8]([C:19]2[N:20]([C:35]([O:37][C:38]([CH3:41])([CH3:40])[CH3:39])=[O:36])[C:21]3[C:26]([CH:27]=2)=[CH:25][C:24]([CH2:28][N:29]2[CH2:34][CH2:33][CH2:32][CH2:31][CH2:30]2)=[CH:23][CH:22]=3)=[C:7]2[C:3]=1[CH2:4][NH:5][C:6]2=[O:42].B1(C=C)OB([CH:49]=[CH2:50])OB(C=C)O1.C1C=CN=CC=1.C(=O)([O-])[O-].[K+].[K+].O>C(COC)OC>[Cl:1][C:2]1[C:10]([CH:49]=[CH2:50])=[CH:9][C:8]([C:19]2[N:20]([C:35]([O:37][C:38]([CH3:39])([CH3:40])[CH3:41])=[O:36])[C:21]3[C:26]([CH:27]=2)=[CH:25][C:24]([CH2:28][N:29]2[CH2:34][CH2:33][CH2:32][CH2:31][CH2:30]2)=[CH:23][CH:22]=3)=[C:7]2[C:3]=1[CH2:4][NH:5][C:6]2=[O:42]Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Procedure
In a similar manner to Step 1 of Example 152, 4-chloro-5-trifluoromethanesulfonyloxy-7-[1-(tert-butoxycarbonyl)-5-(piperidin-1-ylmethyl)indol-2-yl]isoindolinone (70.0 mg, 0.111 mmol) was dissolved in dimethoxyethane (3.5 mL), and the solution was treated with 2,4,6-trivinylcyclotriboroxane-pyridine complex (53.6 mg, 0.222 mmol), [bis(diphenylphosphino)ferrocene]dichloropalladium (7.3 mg, 0.0090 mmol), potassium carbonate (76.7 mg, 0.355 mmol) and water (0.060 mL), followed by purification by preparative thin-layer chromatography (chloroform/methanol=9/1) to obtain 4-chloro-5-vinyl-7-[1-(tert-butoxycarbonyl)-5-(piperidin-1-ylmethyl)indol-2-yl]isoindolinone (33.6 mg, yield 60%).
Workup
- customfollowed by purification by preparative thin-layer chromatography (chloroform/methanol=9/1)
Sources & evidence
- ORD record
- ord-8fb0f853c1be4d52a11d22329c0ddd66
- Source dataset
- uspto-grants-2010_06
- Patent number
- US07745641B2
Linked notes
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