3-Pyridinemethanol → HCID 23028593, compound

HRID 748766Notes

Reaction equation

HRID 748766 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]=[C:22]([CH2:26]O)[CH:21]=1.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:22]2[CH:21]=[N:20][CH:25]=[CH:24][CH:23]=2)(=[O:10])=[O:9])=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 75103-PyridinemethanolHCID 8058HexaneHCID 4622928CyanomethylenetributylphosphoraneHCID 99010282-(((4-Chlorophenyl)sulfonyl)methyl)-1,4-difluorobenzene

Product 1

HCID 23028593HCID 23028593, compoundYield 58%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 21226206Ethyl acetate hexaneSolvent

Procedure

Under an argon atmosphere, the 2-[(4-chlorophenyl)sulfonylmethyl]-1,4-difluorobenzene (120 mg, 0.396 mmol) obtained in Example 5 and 3-pyridylmethanol (50.1 μl, 0.515 mmol) were dissolved in toluene (4 ml), followed by the addition of cyanomethylenetri-n-butylphosphorane (124 mg, 0.515 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=3:7 eluate was concentrated. The solid thus obtained was recrystallized from ethyl acetate-hexane, whereby the title compound (90.3 mg, 0.229 mmol, 58%) was obtained as colorless columnar 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=3:7 eluate was concentrated
  6. customThe solid thus obtained

Sources & evidence

ORD record
ord-ca0b6f81da2b4ce1b68426767a665e81
Source dataset
uspto-grants-2008_07
Patent number
US07399775B2

Reaction notes

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