Potassium Carbonate → HCID 71607960, compound

HRID 1405636Notes

Reaction equation

HRID 1405636 reaction equation
Br[C:2]1[CH:11]=[C:10]2[C:5]([C:6](=[O:34])[N:7]([CH2:14][CH2:15][CH2:16][C@H:17]3[O:21][C:20](=[O:22])[N:19]([C:23]4[CH:24]=[CH:25][C:26]5[S:31][CH2:30][C:29](=[O:32])[NH:28][C:27]=5[CH:33]=4)[CH2:18]3)[C:8](=[O:13])[N:9]2[CH3:12])=[CH:4][CH:3]=1.C([O-])([O-])=O.[K+].[K+].O1CCO[CH2:43][CH2:42]1>O>[CH3:12][N:9]1[C:10]2[C:5](=[CH:4][CH:3]=[C:2]([CH:42]=[CH2:43])[CH:11]=2)[C:6](=[O:34])[N:7]([CH2:14][CH2:15][CH2:16][C@H:17]2[O:21][C:20](=[O:22])[N:19]([C:23]3[CH:24]=[CH:25][C:26]4[S:31][CH2:30][C:29](=[O:32])[NH:28][C:27]=4[CH:33]=3)[CH2:18]2)[C:8]1=[O:13]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 312751,4-DioxaneHCID 71255387HCID 71255387, compound

Product 1

HCID 71607960HCID 71607960, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

A suspension of the compound of Example 46 (0.33 mmol), tetrakis(triphenylphosphine)palladium(0) complex (0.016 mmol), vinylboronic anhydride pyridine complex (0.165 mmol) and K2CO3 (0.33 mmol) in dioxane (2.5 ml) and water (0.8 ml) was purged with argon. The reaction mixture was stirred at 100° C. overnight. The reaction mixture was allowed cooling to rt and was diluted with water and EA. The org. layer was separated and the aq. layer was extracted with EA. The combined org. layers were washed with brine and dried over MgSO4, filtered and concentrated under reduced pressure. The resulting material was sequentially crystallized from TBME/MeOH, EA/MeOH and finally DCM, affording the title compound as colourless crystals in quantitative yield.

Workup

  1. customwas purged with argon
  2. temperatureThe reaction mixture was allowed cooling to rt
  3. additionwas diluted with water and EA
  4. customlayer was separated
  5. extractionthe aq. layer was extracted with EA
  6. washlayers were washed with brine
  7. dry with materialdried over MgSO4
  8. filtrationfiltered
  9. concentrationconcentrated under reduced pressure
  10. customThe resulting material was sequentially crystallized from TBME/MeOH, EA/MeOH and finally DCM

Sources & evidence

ORD record
ord-57765918a0d348b29b65297edc14dda1
Source dataset
uspto-grants-2014_12
Patent number
US08916573B2

Reaction notes

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