Triethylamine → ethyl 2-(1-(4-cyanonaphthalen-1-yl)-1H-imidazol-2-ylthio)-2,2-difluoroacetate

HRID 216607Notes

Reaction equation

HRID 216607 reaction equation
C(N(CC)CC)C.Br[C:9]([F:16])([F:15])[C:10]([O:12][CH2:13][CH3:14])=[O:11].[SH:17][C:18]1[N:19]([C:23]2[C:32]3[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=3)[C:26]([C:33]#[N:34])=[CH:25][CH:24]=2)[CH:20]=[CH:21][N:22]=1>ClCCl>[C:33]([C:26]1[C:27]2[C:32](=[CH:31][CH:30]=[CH:29][CH:28]=2)[C:23]([N:19]2[CH:20]=[CH:21][N:22]=[C:18]2[S:17][C:9]([F:16])([F:15])[C:10]([O:12][CH2:13][CH3:14])=[O:11])=[CH:24][CH:25]=1)#[N:34]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 69585Ethyl bromodifluoroacetateHCID 178510004HCID 178510004, compound

Product 1

HCID 59225900ethyl 2-(1-(4-cyanonaphthalen-1-yl)-1H-imidazol-2-ylthio)-2,2-difluoroacetate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Triethylamine (1.1 eq), followed by ethyl 2-bromo-2,2-difluoroacetate (1.05 eq) were added to a stirring slurry of 4-(2-mercapto-1H-imidazol-1-yl)-1-naphthonitrile (prepared as described herein, 1 eq) in dichloromethane and stirring continued for 3 h. The mixture was washed with aqueous HCl solution (0.2M), 50% saturated sodium chloride solution, dried over sodium sulfate, filtered, and concentrated. Hexanes were added and the mixture concentrated to provide ethyl 2-(1-(4-cyanonaphthalen-1-yl)-1H-imidazol-2-ylthio)-2,2-difluoroacetate.

Workup

  1. customprepared
  2. washThe mixture was washed with aqueous HCl solution (0.2M), 50% saturated sodium chloride solution
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. additionHexanes were added
  7. concentrationthe mixture concentrated

Sources & evidence

ORD record
ord-2b0a786148ad47b296e6e9cc67051798
Source dataset
uspto-grants-2012_06
Patent number
US08193234B2

Reaction notes

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