Tetrabutylammonium Fluoride → {4-[2-Hydroxy-2-(4-iodo-2-methoxy-pyridin-3-yl)-ethyl]-3-nitro-phenyl}-carbamic acid tert-butyl ester
Reaction equation
[F-].C([N+](CCCC)(CCCC)CCCC)CCC.[C:19]([O:23][C:24](=[O:40])[NH:25][C:26]1[CH:31]=[CH:30][C:29]([CH2:32][Si](C)(C)C)=[C:28]([N+:37]([O-:39])=[O:38])[CH:27]=1)([CH3:22])([CH3:21])[CH3:20].[I:41][C:42]1[C:47]([CH:48]=[O:49])=[C:46]([O:50][CH3:51])[N:45]=[CH:44][CH:43]=1>C1COCC1>[C:19]([O:23][C:24](=[O:40])[NH:25][C:26]1[CH:31]=[CH:30][C:29]([CH2:32][CH:48]([OH:49])[C:47]2[C:46]([O:50][CH3:51])=[N:45][CH:44]=[CH:43][C:42]=2[I:41])=[C:28]([N+:37]([O-:39])=[O:38])[CH:27]=1)([CH3:22])([CH3:21])[CH3:20]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
The resultant (3-nitro-phenyl)-carbamic acid tert-butyl ester 2 can then be placed into solution with THF and reacted with ((trimethylsilyl)methyl)magnesiumchloride. A solution of 2,3-dichloro-5,6-dicyano-1,4-benzoquinone in THF can then be added and allowed to react under conditions known to a skilled artisan to afford (3-nitro-4-trimethylsilanylmethyl-phenyl)-carbamic acid tert-butyl ester 3. Tetra-butylammonium fluoride can then be added to a solution of ester 3 and 4-iodo-2-methoxynicotinaldehyde in THF to afford {4-[2-hydroxy-2-(4-iodo-2-methoxy-pyridin-3-yl)-ethyl]-3-nitro-phenyl}-carbamic acid tert-butyl ester 4. A solution of compound 4, in turn, can be added to 2,2,2-trifluoroacetic anhydride and allowed to react to afford trifluoro-acetic acid 2-(4-tert-butoxycarbonyl-amino-2-nitro-phenyl)-1-(4-iodo-2-methoxy-pyridin-3-yl)-ethyl ester 5.
Sources & evidence
- ORD record
- ord-1f3ab013999f4cd4a49f97893873d9fa
- Source dataset
- uspto-grants-2016_07
- Patent number
- US09388166B2
Reaction notes
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