Acetonitrile → HCID 23114828, compound

HRID 2080529Notes

Reaction equation

HRID 2080529 reaction equation
O1CCCC1.[F-].[CH2:7]([N+:11](CCCC)(CCCC)CCCC)CCC.C(#N)C.Br[CH2:28][C:29]1[CH:34]=[C:33]([CH:35]([S:44][C:45]2[CH:50]=[CH:49][C:48]([Cl:51])=[CH:47][CH:46]=2)[C:36]2[CH:41]=[C:40]([F:42])[CH:39]=[CH:38][C:37]=2[F:43])[C:32]([Cl:52])=[CH:31][N:30]=1>CCCCCC>[Cl:52][C:32]1[C:33]([CH:35]([S:44][C:45]2[CH:50]=[CH:49][C:48]([Cl:51])=[CH:47][CH:46]=2)[C:36]2[CH:41]=[C:40]([F:42])[CH:39]=[CH:38][C:37]=2[F:43])=[CH:34][C:29]([CH2:28][C:7]#[N:11])=[N:30][CH:31]=1

Participants

6

Reactant 4

HCID 6342AcetonitrileHCID 8028TetrahydrofuranHCID 2724141Tetrabutylammonium FluorideHCID 23114570HCID 23114570, compound

Product 1

HCID 23114828HCID 23114828, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Procedure

Under an argon atmosphere, trimethylsilylnitrile (0.226 ml, 1.63 mmol) and a tetrahydrofuran solution (1M, 1.63 ml, 1.63 mmol) of tetrabutylammonium fluoride were added sequentially to an acetonitrile (10 ml) solution of 2-bromomethyl-5-chloro-4-[(4-chlorophenylthio)(2,5-difluorophenyl)methyl]pyridine (516 mg, 1.09 mmol) at room temperature. The resulting mixture was stirred for 30 minutes. The reaction mixture was concentrated under reduced pressure. The residue thus obtained was subjected to flash silica gel column chromatography. The fraction obtained from the hexane:ethyl acetate=9:1 eluate was concentrated under reduced pressure to give the title compound (390 mg, 0.93 mmol, 85%) as a brown oil.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. customThe residue thus obtained
  3. concentrationethyl acetate=9:1 eluate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-f5d8c0cf4b504bd18b13e9fb6a94a87f
Source dataset
uspto-grants-2011_04
Patent number
US07932271B2

Reaction notes

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