1,2-Dimethoxyethane → HCID 68897965, compound

HRID 1993728Notes

Reaction equation

HRID 1993728 reaction equation
C(=O)([O-])[O-].[Na+].[Na+].[C:7]([O:10][C@@H:11]1[C@@H:28]([O:29][C:30](=[O:32])[CH3:31])[C@H:27]([O:33][C:34](=[O:36])[CH3:35])[CH2:26][S:25][CH:12]1[O:13][C:14]1[C:15]2[N:16]([CH:20]=[C:21]([CH2:23]Cl)[N:22]=2)[CH:17]=[CH:18][CH:19]=1)(=[O:9])[CH3:8].CO[CH2:39][CH2:40]OC>O.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[C:7]([O:10][C@@H:11]1[C@@H:28]([O:29][C:30](=[O:32])[CH3:31])[C@H:27]([O:33][C:34](=[O:36])[CH3:35])[CH2:26][S:25][C@H:12]1[O:13][C:14]1[C:15]2[N:16]([CH:20]=[C:21]([CH2:23][C:40]3[CH:39]=[CH:27][CH:28]=[CH:11][CH:12]=3)[N:22]=2)[CH:17]=[CH:18][CH:19]=1)(=[O:9])[CH3:8]

Participants

6

Reactant 3

HCID 80711,2-DimethoxyethaneHCID 10340Sodium CarbonateHCID 68899570HCID 68899570, compound

Product 1

HCID 68897965HCID 68897965, compoundYield 42%

Reagents, catalysts & solvents 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 962WaterSolvent2×

Conditions

Temperature
120 °C

Procedure

A solution of 0.108 g (1.02 mM) of sodium carbonate in 2 ml of water, 0.055 g (0.0678 mM) of [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium (II) dichloromethane and 0.277 g (1.35 mM) of 4,4,5,5-tetramethyl-2-phenyl-1,2,3-dioxaborolane are added to a solution of 0.31 g (0.678 mM) of 2-chloromethylimidazo[1,2-α]pyridin-8-yl 2,3,4-tri-O-acetyl-5-thio-D-xylopyranoside obtained according to example 31, in 4 ml of DME. The reaction mixture is microwave-heated at 120° C. for 30 minutes. After cooling, water is added and the resulting mixture is extracted with ethyl acetate. The organic phase is dried over sodium sulfate and is concentrated under reduced pressure. The evaporation residue is purified by silica gel chromatography, elution being carried out with a dichloromethane/methanol mixture (97/3; v/v), and then crystallized from ether. The expected product is obtained in the form of a white solid with a yield of 42%.

Workup

  1. customobtained
  2. temperatureAfter cooling
  3. extractionthe resulting mixture is extracted with ethyl acetate
  4. dry with materialThe organic phase is dried over sodium sulfate
  5. concentrationis concentrated under reduced pressure
  6. customThe evaporation residue is purified by silica gel chromatography, elution
  7. customcrystallized from ether

Sources & evidence

ORD record
ord-f2b8395fbd3d46b0af323c9e2b0a8f1c
Source dataset
uspto-grants-2010_01
Patent number
US07652032B2

Reaction notes

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