1,2-Dimethoxyethane → 6-(4-(Methylsulfonyl)phenyl)pyridin-3-ol

HRID 423663Notes

Reaction equation

HRID 423663 reaction equation
Br[C:2]1[N:7]=[CH:6][C:5]([OH:8])=[CH:4][CH:3]=1.[CH3:9][S:10]([C:13]1[CH:18]=[CH:17][C:16](B(O)O)=[CH:15][CH:14]=1)(=[O:12])=[O:11].C([O-])([O-])=O.[Na+].[Na+].COCCOC>CCOC(C)=O.O.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[CH3:9][S:10]([C:13]1[CH:18]=[CH:17][C:16]([C:2]2[N:7]=[CH:6][C:5]([OH:8])=[CH:4][CH:3]=2)=[CH:15][CH:14]=1)(=[O:12])=[O:11]

Participants

8

Reactant 4

HCID 80711,2-DimethoxyethaneHCID 10340Sodium CarbonateHCID 27343644-(Methanesulfonyl)phenylboronic acidHCID 27628652-Bromo-5-hydroxypyridine

Product 1

HCID 532295926-(4-(Methylsulfonyl)phenyl)pyridin-3-olYield 29.1%

Reagents, catalysts & solvents 3

HCID 178418476HCID 178418476, compoundCatalystHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 6-bromo-3-pyridinol (7 g, 40 mmol), [4-(methylsulfonyl)phenyl]boronic acid (8 g, 40 mmol), 2M Na2CO3 (30 mL), PdCl2(PPh3)2 (1 g) and DME (60 mL) under N2 was heated at 80° C. overnight. The reaction was allowed to cool to room temperature and was diluted with EtOAc and water. The resulting precipitate was filtered off and the aqueous layer was extracted with EtOAc. The combined organic extracts were dried over MgSO4, filtered and concentrated. The aqueous phase was also concentrated. Each of the residues was recrystallized from MeOH. The solid material from the organic phase recrystallization and the mother liquors from both aqueous and organic recrystallizations were combined, concentrated and purified by chromatography on a silica gel column using 0 to 10% MeOH/CH2Cl2 to give 6-[4-(methylsulfonyl)phenyl]-3-pyridinol (2.9 g, 29%) as a tan solid.

Workup

  1. temperatureto cool to room temperature
  2. filtrationThe resulting precipitate was filtered off
  3. extractionthe aqueous layer was extracted with EtOAc
  4. dry with materialThe combined organic extracts were dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. concentrationThe aqueous phase was also concentrated
  8. customEach of the residues was recrystallized from MeOH
  9. customThe solid material from the organic phase recrystallization
  10. customthe mother liquors from both aqueous and organic recrystallizations
  11. concentrationconcentrated
  12. custompurified by chromatography on a silica gel column

Sources & evidence

ORD record
ord-6c50aa27fb8e43cd8c26c26e7142067d
Source dataset
uspto-grants-2012_01
Patent number
US08101634B2

Reaction notes

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