Reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]([CH2:13][C:14](=[CH2:20])[CH2:15][CH2:16][N:17]=[N+]=[N-])[S:9]([CH3:12])(=[O:11])=[O:10])=[C:4](I)[CH:3]=1.C[Si]([SiH]([Si](C)(C)C)[Si](C)(C)C)(C)C.N(C1(C#N)CCCCC1)=NC1(C#N)CCCCC1>C1C=CC=CC=1>[CH3:12][S:9]([N:8]1[C:5]2[C:4](=[CH:3][C:2]([Cl:1])=[CH:7][CH:6]=2)[C:14]2([CH2:15][CH2:16][NH:17][CH2:20]2)[CH2:13]1)(=[O:11])=[O:10]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
A degassed solution of N-(4-Chloro-2-iodo-phenyl)-N-(4-azido-2-methylene-butyl)-methanesulfonamide (1.38 g) in benzene (200 ml) was heated to reflux under argon. Tris(trimethylsilyl)silane (1.32 ml) was added dropwise followed by 1,1′-azobis(cyclohexane carbonitrile) (110 mg). The reaction mixture was stirred at reflux for 20 hours then concentrated in vacuo. The residue was dissolved in ethyl acetate (60 ml), extracted with HC12N (3×60 ml). The aqueous layer was basified with 2N sodium hydroxide (250 ml) then extracted with ethyl acetate (3×150 ml). The combined organic layers were dried over sodium sulfate and the solvent evaporated in vacuo to afford 1-methanesulfonyl-5-chloro-spiro[indoline-3,3′-pyrrolidine] (766 mg) which was used as such for the next step.
Workup
- temperatureto reflux under argon
- temperatureat reflux for 20 hours
- concentrationthen concentrated in vacuo
- dissolutionThe residue was dissolved in ethyl acetate (60 ml)
- extractionextracted with HC12N (3×60 ml)
- extractionthen extracted with ethyl acetate (3×150 ml)
- dry with materialThe combined organic layers were dried over sodium sulfate
- customthe solvent evaporated in vacuo
Sources & evidence
- ORD record
- ord-bc70f85125c042febb33b40f444865ce
- Source dataset
- uspto-grants-2014_09
- Patent number
- US08846907B2
Linked notes
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