Water → 5-{5-[5-Fluoro-2-(methyloxy)-3-(2-oxoethyl)phenyl]-1,3,4-thiadiazol-2-yl}-2-(2-methylpropyl)benzonitrile

HRID 1942613Notes

Reaction equation

HRID 1942613 reaction equation
[F:1][C:2]1[CH:3]=[C:4](/[CH:27]=[CH:28]/[O:29]C)[C:5]([O:25][CH3:26])=[C:6]([C:8]2[S:12][C:11]([C:13]3[CH:14]=[CH:15][C:16]([CH2:21][CH:22]([CH3:24])[CH3:23])=[C:17]([CH:20]=3)[C:18]#[N:19])=[N:10][N:9]=2)[CH:7]=1.[I-].[Na+].C[Si](Cl)(C)C.O>C(#N)C>[F:1][C:2]1[CH:3]=[C:4]([CH2:27][CH:28]=[O:29])[C:5]([O:25][CH3:26])=[C:6]([C:8]2[S:12][C:11]([C:13]3[CH:14]=[CH:15][C:16]([CH2:21][CH:22]([CH3:24])[CH3:23])=[C:17]([CH:20]=3)[C:18]#[N:19])=[N:10][N:9]=2)[CH:7]=1

Participants

6

Reactant 4

HCID 962WaterHCID 5238Sodium IodideHCID 6397ChlorotrimethylsilaneHCID 669817285-(5-{5-fluoro-2-(methyloxy)-3-[(E)-2-(methyloxy)ethenyl]phenyl}-1,3,4-thiadiazol-2-yl)-2-(2-methylpropyl)benzonitrile

Product 1

HCID 866590035-{5-[5-Fluoro-2-(methyloxy)-3-(2-oxoethyl)phenyl]-1,3,4-thiadiazol-2-yl}-2-(2-methylpropyl)benzonitrileYield 59.7%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of 5-(5-{5-fluoro-2-(methyloxy)-3-[(E)-2-(methyloxy)ethenyl]phenyl}-1,3,4-thiadiazol-2-yl)-2-(2-methylpropyl)benzonitrile (D36) (130 mg) and sodium iodide (92 mg) in acetonitrile (20 mL) stirred under nitrogen at room temperature was added TMSCl (0.078 mL) dropwise. The reaction mixture was stirred at room temperature for 10 min. Water was added. The aqueous solution was extracted with EA for 3 times. The organic phase was washed with saturated Na2S2O3 solution and saturated brine, dried over sodium sulphate and evaporated in vacuo to afford the crude product 5-{5-[5-fluoro-2-(methyloxy)-3-(2-oxoethyl)phenyl]-1,3,4-thiadiazol-2-yl}-2-(2-methylpropyl)benzonitrile (D37) (75 mg) as a yellow oil. MS (ES): C22H20FN3O2S requires 409. found 410.2 (M+H+).

Workup

  1. extractionThe aqueous solution was extracted with EA for 3 times
  2. washThe organic phase was washed with saturated Na2S2O3 solution and saturated brine
  3. dry with materialdried over sodium sulphate
  4. customevaporated in vacuo

Sources & evidence

ORD record
ord-b1b3c56857684e83bdcd253f26ec746c
Source dataset
uspto-grants-2013_03
Patent number
US08389508B2

Reaction notes

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