1,2-Dimethoxyethane → HCID 44196090, compound

HRID 1685441Notes

Reaction equation

HRID 1685441 reaction equation
C([O:4][C@@H:5]1[C@@H:18]([O:19]C(=O)C)[C@H:17]([O:23]C(=O)C)[CH2:16][S:15][C@H:6]1[O:7][C:8]1[C:9](Br)=[N:10][CH:11]=[CH:12][CH:13]=1)(=O)C.[CH3:27][O:28][C:29]1[CH:34]=[CH:33][C:32](B(O)O)=[CH:31][CH:30]=1.C(=O)([O-])[O-].[Cs+].[Cs+].COCCOC>CO>[O:7]([C:8]1[C:9]([C:32]2[CH:33]=[CH:34][C:29]([O:28][CH3:27])=[CH:30][CH:31]=2)=[N:10][CH:11]=[CH:12][CH:13]=1)[C@@H:6]1[S:15][CH2:16][C@@H:17]([OH:23])[C@H:18]([OH:19])[C@H:5]1[OH:4]

Participants

6

Reactant 4

HCID 80711,2-DimethoxyethaneHCID 10796Cesium carbonateHCID 201262(4-Methoxyphenyl)boronic acidHCID 12136256HCID 12136256, compound

Product 1

HCID 44196090HCID 44196090, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of 0.8 g (1.8 mM) of the 2-bromo-3-pyridinyl 2,3,4-tri-O-acetyl-5-thio-β-D-xylopyranoside obtained according to Preparation 28, 0.325 g (2.14 mM) of 4-methoxyphenylboronic acid, 0.8 g (0.08 mM) of Suzuki's catalyst supported on resin (Argonaut, PSPPh3Pd resin), 1.16 g (3.56 mM) of cesium carbonate, 5 ml of DME and 4 ml of methanol is placed in a reactor adapted for microwaves. The mixture is heated at 120° C. for 30 minutes by microwaves. After filtration, rinsing with methanol and evaporation of the solvents, the residue obtained is chromatographed directly on silica gel using firstly pure dichloro-methane and then a dichloromethane/methanol mixture (9/1; v/v) as the eluent. The foam obtained is crystallized from ether to give the expected product in the form of a white powder (yield=65%).

Workup

  1. customobtained
  2. customis placed in a reactor
  3. filtrationAfter filtration
  4. washrinsing with methanol and evaporation of the solvents
  5. customthe residue obtained
  6. customis chromatographed directly on silica gel using firstly pure dichloro-methane
  7. customThe foam obtained
  8. customis crystallized from ether

Sources & evidence

ORD record
ord-95645d80c49246209de34a32c0bda8a6
Source dataset
uspto-grants-2012_04
Patent number
US08148407B2

Reaction notes

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