Dichloromethane → 6-(2-Methoxy-3-pyridinyl)-3-pyridinyl 2,3,4-tri-O-acetyl-5-thio-beta-D-xylo-pyranoside

HRID 419790Notes

Reaction equation

HRID 419790 reaction equation
C(=O)([O-])[O-].[Na+].[Na+].ClCCl.[CH3:10][O:11][C:12]1[C:17](B(O)O)=[CH:16][CH:15]=[CH:14][N:13]=1.[C:21]([O:24][C@@H:25]1[C@@H:38]([O:39][C:40](=[O:42])[CH3:41])[C@H:37]([O:43][C:44](=[O:46])[CH3:45])[CH2:36][S:35][C@H:26]1[O:27][C:28]1[CH:29]=[N:30][C:31](Br)=[CH:32][CH:33]=1)(=[O:23])[CH3:22]>O.COCCOC>[C:21]([O:24][C@@H:25]1[C@@H:38]([O:39][C:40](=[O:42])[CH3:41])[C@H:37]([O:43][C:44](=[O:46])[CH3:45])[CH2:36][S:35][C@H:26]1[O:27][C:28]1[CH:29]=[N:30][C:31]([C:17]2[C:12]([O:11][CH3:10])=[N:13][CH:14]=[CH:15][CH:16]=2)=[CH:32][CH:33]=1)(=[O:23])[CH3:22]

Participants

7

Reactant 4

HCID 6344DichloromethaneHCID 10340Sodium CarbonateHCID 2762709(2-Methoxypyridin-3-yl)boronic acidHCID 866250296-bromo-3-pyridinyl 2,3,4-tri-O-acetyl-5-thio-beta-D-xylopyranoside

Product 1

HCID 666510396-(2-Methoxy-3-pyridinyl)-3-pyridinyl 2,3,4-tri-O-acetyl-5-thio-beta-D-xylo-pyranosideYield 70%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 80711,2-DimethoxyethaneSolvent

Procedure

A solution of 0.354 g (3.34 mM) of sodium carbonate in 3 ml of water, 0.18 g (0.223 mM) of the [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II) complex with dichloromethane and 0.68 g (4.46 mM) of 2-methoxy-3-pyridineboronic acid are added to a solution of 1 g (2.23 mM) of 6-bromo-3-pyridinyl 2,3,4-tri-O-acetyl-5-thio-β-D-xylopyranoside, obtained according to preparation IV, in 10 ml of DME. The reaction mixture is heated using microwave radiation at 120° C. for 20 minutes and cooled, water is added and extraction is carried out with ethyl acetate. The organic phase is washed with a 1M sodium carbonate solution and then with water to neutral pH, dried over magnesium sulfate and concentrated under reduced pressure. The evaporation residue is purified by chromatography on a silica column (eluent: toluene/acctone 90/10; v/v) in order to obtain the expected product in the form of a white solid with a yield of 70%.

Workup

  1. customobtained
  2. temperatureThe reaction mixture is heated
  3. customat 120° C.
  4. customfor 20 minutes
  5. temperaturecooled
  6. extractionextraction
  7. washThe organic phase is washed with a 1M sodium carbonate solution
  8. dry with materialwith water to neutral pH, dried over magnesium sulfate
  9. concentrationconcentrated under reduced pressure
  10. customThe evaporation residue is purified by chromatography on a silica column (eluent: toluene/acctone 90/10; v/v) in order

Sources & evidence

ORD record
ord-1c76bab32a5642dab9a07480d3a7badf
Source dataset
uspto-grants-2012_01
Patent number
US08093394B2

Reaction notes

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