Phosgene → 4-[3-(2-Bromo-4-fluorobenzyl)-4,4-dimethyl-2,5-dioxoimidazolidin-1-yl]-2-methylbenzonitrile
Reaction equation
[CH3:1][C:2]1[CH:9]=[C:8]([N+:10]([O-])=O)[CH:7]=[CH:6][C:3]=1[C:4]#[N:5].I.NC1C=CC(C#N)=C(C)C=1.Cl.[NH2:25][C:26]([CH3:35])([CH3:34])[C:27]([O:29]C(C)(C)C)=O.[C:36](Cl)(Cl)=[O:37].[Br:40][C:41]1[CH:46]=[C:45]([F:47])[CH:44]=[CH:43][C:42]=1[CH2:48]Br>>[Br:40][C:41]1[CH:46]=[C:45]([F:47])[CH:44]=[CH:43][C:42]=1[CH2:48][N:25]1[C:26]([CH3:34])([CH3:35])[C:27](=[O:29])[N:10]([C:8]2[CH:7]=[CH:6][C:3]([C:4]#[N:5])=[C:2]([CH3:1])[CH:9]=2)[C:36]1=[O:37]Participants
Reactant 6
Product 1
Procedure
In the synthesis of the compound of example 160, the procedure was as in the preparation of the compound of example 158: 2-methyl-4-nitrobenzonitrile was reduced with hydriodic acid (analogously to the procedure for the synthesis of compound 63.4) to 4-amino-2-methylbenzonitrile (160.3; 1H NMR: 7.3, d, 1H, 6.48, s, 1H, 6.42, d, 1H, 6.02, s, 2H; 227, s, 3H). The aniline 160.3 was converted with standard methods using tert-butyl 2-amino-2-methylpropionate hydrochloride and phosgene (solution in toluene) to compound 160.1 (4-(4,4-dimethyl-2,5-dioxoimidazolidin-1-yl)-2-methylbenzonitrile; 1H NMR: 8.7, s, 1H, 7.88, d, 1H, 7.55, s, 1H; 7.44, d, 1H, 1.4, s, 3H), which was in turn reacted with 2-bromo-1-bromomethyl-4-fluorobenzene to give 160.2 (4-[3-(2-bromo-4-fluorobenzyl)-4,4-dimethyl-2,5-dioxoimidazolidin-1-yl]-2-methylbenzonitrile; molecular weight 429.04 (C20H17BrFN3O2);
Sources & evidence
- ORD record
- ord-08d7b563b5914d2ba33a75e572ca3083
- Source dataset
- uspto-grants-2010_07
- Patent number
- US07759366B2
Reaction notes
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