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

HRID 748767Notes

Reaction equation

HRID 748767 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][C:23]([CH2:26]O)=[CH:22][CH:21]=1.C(C=P(CCCC)(CCCC)CCCC)#N.CCCCCC>C1(C)C=CC=CC=1.C(OCC)(=O)C>[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:23]2[CH:24]=[CH:25][N:20]=[CH:21][CH:22]=2)(=[O:10])=[O:9])=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 8058HexaneHCID 114724-HydroxymethylpyridineHCID 4622928CyanomethylenetributylphosphoraneHCID 99010282-(((4-Chlorophenyl)sulfonyl)methyl)-1,4-difluorobenzene

Product 1

HCID 597509354-[2-[(4-Chlorophenyl)sulfonyl]-2-(2,5-difluorophenyl)ethyl]pyridineYield 31.4%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Procedure

Under an argon atmosphere, the 2-[(4-chlorophenyl)sulfonylmethyl]-1,4-difluorobenzene (200 mg, 0.660 mmol) obtained in Example 5 and 4-pyridylmethanol (144 mg, 1.32 mmol) were dissolved in toluene (6 ml), followed by the addition of cyanomethylenetri-n-butylphosphorane (318 mg, 1.32 mmol). The resulting mixture was heated under reflux for 15 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=1:2 elulate was concentrated. The solid thus obtained was recrystallized from ethyl acetate, whereby the title compound (81.4 mg, 0.207 mmol, 31%) was obtained as colorless needle crystals.

Workup

  1. temperatureThe resulting mixture was heated
  2. temperatureunder reflux for 15 hours under an argon atmosphere
  3. concentrationThe reaction mixture was then concentrated
  4. customThe residue thus obtained
  5. concentrationethyl acetate=1:2 elulate was concentrated
  6. customThe solid thus obtained

Sources & evidence

ORD record
ord-081e23250dd54f8faca5707d636f88d5
Source dataset
uspto-grants-2008_07
Patent number
US07399775B2

Reaction notes

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