Hexane → 2-[2-[(4-Chlorophenyl)sulfonyl]-2-(2,5-difluorophenyl)ethyl]pyridine

HRID 748765Notes

Reaction equation

HRID 748765 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([CH2:11][C:12]2[CH:17]=[C:16]([F:18])[CH:15]=[CH:14][C:13]=2[F:19])(=[O:10])=[O:9])=[CH:4][CH:3]=1.[N:20]1[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=1[CH2:26]O.C(C=P(CCCC)(CCCC)CCCC)#N.CCCCCC>C1(C)C=CC=CC=1.C(OCC)(=O)C.CCCCCC>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([CH:11]([C:12]2[CH:17]=[C:16]([F:18])[CH:15]=[CH:14][C:13]=2[F:19])[CH2:26][C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][N:20]=2)(=[O:10])=[O:9])=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 8058HexaneHCID 11474PiconolHCID 4622928CyanomethylenetributylphosphoraneHCID 99010282-(((4-Chlorophenyl)sulfonyl)methyl)-1,4-difluorobenzene

Product 1

HCID 597508772-[2-[(4-Chlorophenyl)sulfonyl]-2-(2,5-difluorophenyl)ethyl]pyridineYield 49.5%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 21226206Ethyl acetate hexaneSolvent

Procedure

Under an argon atmosphere, the 2-[(4-chlorophenyl)sulfonylmethyl]-1,4-difluorobenzene (150 mg, 0.495 mmol) obtained in Example 5 and 2-pyridylmethanol (95.5 μl, 0.990 mmol) were dissolved in toluene (5 ml), followed by the addition of cyanomethylenetri-n-butylphosphorane (239 mg, 0.990 mmol). The resulting mixture was heated under reflux for 18 hours under an argon atmosphere. The reaction mixture was then concentrated. The residue thus obtained was subjected to flash chromatography on a silica gel column, and the fraction obtained from the hexane:ethyl acetate=1:1 eluate was concentrated. The solid thus obtained was recrystallized from ethyl acetate-hexane, whereby the title compound (96.6 mg, 0.245 mmol, 49%) was obtained as colorless needle crystals.

Workup

  1. temperatureThe resulting mixture was heated
  2. temperatureunder reflux for 18 hours under an argon atmosphere
  3. concentrationThe reaction mixture was then concentrated
  4. customThe residue thus obtained
  5. concentrationethyl acetate=1:1 eluate was concentrated
  6. customThe solid thus obtained

Sources & evidence

ORD record
ord-3b86339055a44d51895acad42f6e3a6f
Source dataset
uspto-grants-2008_07
Patent number
US07399775B2

Reaction notes

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