3-Hydroxypyridine → HCID 12136232, compound

HRID 2377582Notes

Reaction equation

HRID 2377582 reaction equation
[OH:1][C:2]1[CH:3]=[N:4][CH:5]=[CH:6][CH:7]=1.[C:8]([O:11][C@@H:12]1[C@@H:17]([O:18][C:19](=[O:21])[CH3:20])[C@H:16]([O:22][C:23](=[O:25])[CH3:24])[CH2:15][S:14][C@@H:13]1Br)(=[O:10])[CH3:9]>C1(C)C=CC=CC=1.C(#N)C.[Cl-].[Zn+2].[Cl-].[N-]1C=CN=C1.[Ag+]>[C:8]([O:11][C@@H:12]1[C@@H:17]([O:18][C:19](=[O:21])[CH3:20])[C@H:16]([O:22][C:23](=[O:25])[CH3:24])[CH2:15][S:14][C@H:13]1[O:1][C:2]1[CH:3]=[N:4][CH:5]=[CH:6][CH:7]=1)(=[O:10])[CH3:9]

Participants

7

Reactant 2

HCID 79713-HydroxypyridineHCID 109263142,3,4-tri-O-acetyl-5-thio-alpha-xylopyranosyl bromide

Product 1

HCID 12136232HCID 12136232, compoundYield 37.4%

Reagents, catalysts & solvents 4

HCID 3007855ZincchlorideCatalystHCID 10931941Silver imidazolateCatalystHCID 1140TolueneSolventHCID 6342AcetonitrileSolvent

Conditions

Temperature
60 °C

Procedure

2.15 g (15.8 mmol) of anhydrous zinc chloride, 1 g (10.5 mmol) of 3-hydroxy-pyridine and 3 g of 13X molecular sieve are mixed in 10 ml of toluene and 10 ml of acetonitrile. The mixture is stirred for 15 min and then heated to 60° C. and placed in the dark. 2.2 g (12.6 mmol) of silver imidazolate and 4.5 g (12.6 mmol) of 2,3,4-tri-O-acetyl-5-thio-α-D-xylopyranosyl bromide are added. The mixture is stirred for 18 hours at 60° C. and then filtered. 50 ml of ethyl acetate are added to the filtrate and the organic phase is washed with 1 N sodium hydroxide solution. (A flocculation is observed, which is removed by filtration on a bed of filter aid.) The organic phase is separated off, washed with water and then dried over magnesium sulfate and concentrated under reduced pressure. The residue is crystallized by adding ethyl ether; the crystals obtained are filtered off and dried to give 1.45 g of the expected product in the form of white crystals (yield=37%).

Workup

  1. stirringThe mixture is stirred for 18 hours at 60° C.
  2. filtrationfiltered
  3. addition50 ml of ethyl acetate are added to the filtrate
  4. washthe organic phase is washed with 1 N sodium hydroxide solution
  5. customwhich is removed by filtration on a bed of filter aid
  6. custom) The organic phase is separated off
  7. washwashed with water
  8. dry with materialdried over magnesium sulfate
  9. concentrationconcentrated under reduced pressure
  10. customThe residue is crystallized
  11. additionby adding ethyl ether
  12. customthe crystals obtained
  13. filtrationare filtered off
  14. customdried

Sources & evidence

ORD record
ord-43c60d0ab09e45c295c48f33830ac5fd
Source dataset
uspto-grants-2008_12
Patent number
US07470671B2

Reaction notes

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