Cesium fluoride → HCID 67292650, compound

HRID 1685417Notes

Reaction equation

HRID 1685417 reaction equation
[C:1]([O:4][C@@H:5]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:6]1[O:7][C:8]1[C:9](Cl)=[N:10][CH:11]=[CH:12][CH:13]=1)(=[O:3])[CH3:2].[C:27]1(B(O)O)[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1.[F-].[Cs+]>COCCOC>[C:1]([O:4][C@@H:5]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:6]1[O:7][C:8]1[C:9]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)=[N:10][CH:11]=[CH:12][CH:13]=1)(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 25953Cesium fluorideHCID 66827Phenylboronic AcidHCID 86625025HCID 86625025, compound

Product 1

HCID 67292650HCID 67292650, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
120 °C

Procedure

0.1 g (0.24 mM) of 2-chloro-3-pyridinyl 2,3,4-tri-O-acetyl-5-thio-β-D-xylo-pyranoside, 30 ml of DME, 0.037 g (0.29 mM) of phenylboronic acid, 0.102 g (0.66 mM) of cesium fluoride and 0.021 g (0.024 mM) of [1,1′-bis(diphenyl-phosphino)ferrocene]dichloropalladium(II) dichloromethane are mixed. The mixture is heated for 2 hours at 120° C. under an inert atmosphere in a microwave oven. The reaction medium is then filtered on a Whatman filter, the material on the filter is rinsed with ethyl acetate and the filtrate is extracted. The pH is neutralized with ammonium chloride solution. The organic phase is dried over sodium sulfate and the product is concentrated under reduced pressure. It is purified by chromatography on a silica column (eluent: dichloromethane/ethyl acetate 99/1; v/v) to give the expected product in the form of a white powder with a yield of 90%.

Workup

  1. filtrationThe reaction medium is then filtered on a Whatman
  2. filtrationfilter
  3. washthe material on the filter is rinsed with ethyl acetate
  4. extractionthe filtrate is extracted
  5. dry with materialThe organic phase is dried over sodium sulfate
  6. concentrationthe product is concentrated under reduced pressure
  7. customIt is purified by chromatography on a silica column (eluent: dichloromethane/ethyl acetate 99/1; v/v)

Sources & evidence

ORD record
ord-dd98737b75774db09af13c74ae88fa77
Source dataset
uspto-grants-2012_04
Patent number
US08148407B2

Reaction notes

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