2-Methylpyridin-3-ol → HCID 12136242, compound

HRID 2377583Notes

Reaction equation

HRID 2377583 reaction equation
[CH3:1][C:2]1[C:7]([OH:8])=[CH:6][CH:5]=[CH:4][N:3]=1.[C:9]([O:12][C@@H:13]1[C@@H:18]([O:19][C:20](=[O:22])[CH3:21])[C@H:17]([O:23][C:24](=[O:26])[CH3:25])[CH2:16][S:15][C@@H:14]1Br)(=[O:11])[CH3:10]>C1(C)C=CC=CC=1.C(#N)C.[O-2].[Zn+2].[Cl-].[Zn+2].[Cl-]>[C:9]([O:12][C@@H:13]1[C@@H:18]([O:19][C:20](=[O:22])[CH3:21])[C@H:17]([O:23][C:24](=[O:26])[CH3:25])[CH2:16][S:15][C@H:14]1[O:8][C:7]1[C:2]([CH3:1])=[N:3][CH:4]=[CH:5][CH:6]=1)(=[O:11])[CH3:10]

Participants

7

Reactant 2

HCID 707192-Methylpyridin-3-olHCID 109263142,3,4-tri-O-acetyl-5-thio-alpha-xylopyranosyl bromide

Product 1

HCID 12136242HCID 12136242, compound

Reagents, catalysts & solvents 4

HCID 3007855ZincchlorideCatalystHCID 3007857Zinc OxideCatalystHCID 1140TolueneSolventHCID 6342AcetonitrileSolvent

Conditions

Temperature
60 °C

Procedure

6 g (73.7 mmol) of zinc oxide, 2.6 g (19 mmol) of zinc chloride and 4 g of 4 Å molecular sieve are mixed. This mixture is desiccated perfectly and 2 g (18.3 mmol) of 2-methyl-3-pyridinol and 6.6 g (18.6 mmol) of 2,3,4-tri-O-acetyl-5-thio-α-D-xylopyranosyl bromide in 40 ml of toluene and 40 ml of acetonitrile are then added. The mixture is stirred at 60° C. for 18 hours and then filtered. The filtrate is concentrated under reduced pressure and the evaporation residue is purified by chromatography on silica gel using an ethyl acetate/hexane mixture (7/3 then 100% ethyl acetate; v/v) as the eluent to give the expected product in the form of a beige solid (yield=7%).

Workup

  1. filtrationfiltered
  2. concentrationThe filtrate is concentrated under reduced pressure
  3. customthe evaporation residue is purified by chromatography on silica gel using an ethyl acetate/hexane mixture (7/3

Sources & evidence

ORD record
ord-bb387a39090a48d6957159b6732981b7
Source dataset
uspto-grants-2008_12
Patent number
US07470671B2

Reaction notes

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