Potassium Carbonate → Ethyl 2-((2-chloro-6-fluorophenethyl)thio)-1-(4-fluorophenyl)-1H-imidazole-5-carboxylate

HRID 2368512Notes

Reaction equation

HRID 2368512 reaction equation
F[C:2]1C=CC(N2C(C(N(OC)C)=O)=CN=C2SCC2C(F)=CC=C(F)C=2F)=C[CH:3]=1.[F:30][C:31]1[CH:36]=[CH:35][C:34]([N:37]2[C:41]([C:42]([OH:44])=[O:43])=[CH:40][N:39]=[C:38]2[S:45][C:46](C2C=CC=CC=2)(C2C=CC=CC=2)[C:47]2C=CC=CC=2)=[CH:33][CH:32]=1.CS(OCC[C:72]1[C:77]([F:78])=[CH:76][CH:75]=[CH:74][C:73]=1[Cl:79])(=O)=O.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[Cl:79][C:73]1[CH:74]=[CH:75][CH:76]=[C:77]([F:78])[C:72]=1[CH2:47][CH2:46][S:45][C:38]1[N:37]([C:34]2[CH:33]=[CH:32][C:31]([F:30])=[CH:36][CH:35]=2)[C:41]([C:42]([O:44][CH2:2][CH3:3])=[O:43])=[CH:40][N:39]=1

Participants

6

Reactant 4

HCID 11430Potassium CarbonateHCID 711174681-(4-fluorophenyl)-2-(tritylthio)-1H-imidazole-5-carboxylic acidHCID 866775411-(4-Fluorophenyl)-N-methoxy-N-methyl-2-((2,3,6-trifluorobenzyl)thio)-1H-imidazole-5-carboxamideHCID 866775542-Chloro-6-fluorophenethyl methanesulfonate

Product 1

HCID 71117392Ethyl 2-((2-chloro-6-fluorophenethyl)thio)-1-(4-fluorophenyl)-1H-imidazole-5-carboxylate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Ethyl 2-((2-chloro-6-fluorophenethyl)thio)-1-(4-fluorophenyl)-1H-imidazole-5-carboxylate (53) was prepared in a similar manner as that described for the synthesis of compound 9 using ethyl 1-(4-fluorophenyl)-2-mercapto-1H-imidazole-5-carboxylate (6) (700 mg, 2.62 mmol), 2-chloro-6-fluorophenethyl methanesulfonate (813 mg, 3.144 mmol), potassium carbonate (1.1 g, 7.86 mmol) in DMF (20 mL).

Sources & evidence

ORD record
ord-3b90d7188b654edfae7f26d0770fcc8e
Source dataset
uspto-grants-2014_04
Patent number
US08703776B2

Reaction notes

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