Potassium Carbonate → HCID 86590615, compound

HRID 1825793Notes

Reaction equation

HRID 1825793 reaction equation
[C:1]([O:5][C:6](=[O:31])[NH:7][C:8]1[C:21]2[CH2:20][C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[S:13][C:12]=2[C:11](B2OC(C)(C)C(C)(C)O2)=[CH:10][CH:9]=1)([CH3:4])([CH3:3])[CH3:2].Cl[C:33]1[O:34][C:35]([N:40]2[CH2:45][CH2:44][O:43][CH2:42][CH2:41]2)=[CH:36][C:37](=[O:39])[CH:38]=1.C([O-])([O-])=O.[K+].[K+]>O1CCOCC1>[C:1]([O:5][C:6](=[O:31])[NH:7][C:8]1[C:21]2[CH2:20][C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[S:13][C:12]=2[C:11]([C:33]2[O:34][C:35]([N:40]3[CH2:41][CH2:42][O:43][CH2:44][CH2:45]3)=[CH:36][C:37](=[O:39])[CH:38]=2)=[CH:10][CH:9]=1)([CH3:2])([CH3:3])[CH3:4]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 66052622-Chloro-6-morpholinopyran-4-oneHCID 67524892HCID 67524892, compound

Product 1

HCID 86590615HCID 86590615, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

[4-(4,4,5,5-Tetramethyl-[1,3,2]dioxaborolan-2-yl)-9H-thioxanthen-1-yl]-carbamic acid tert-butyl ester (2.90 g, 6.50 mmol) was introduced to a solution of 2-Chloro-6-morpholin-4-yl-pyran-4-one (3)(1.4 g, 6.50 mmol) in anhydrous dioxane (6 mL). Powdered K2CO3 (2.01 g, 14.50 mmol) was added and the mixture degassed (sonication for 20 mins then saturated with N2). To the degassed solution was added Tetrakis (triphenylphosphine) palladium (0.39 g) before it was degassed for a further 20 minutes. A reflux condenser was attached to the reaction vessel which was submerged into an oil bath maintained at 100° C. for 14 hours whereupon the golden mixture was cooled and diluted with EtOAc (50 ml) and then washed with water (20 ml) and saturated brine (20 ml). Organic extract was dried using MgSO4, filtered and concentrated in vacuo to give the title compound as a light brown oil that was used without further purification. m/z (LC-MS, ESP): 493 [M+H]+, R/T=4.41 mins.

Workup

  1. customthe mixture degassed (
  2. customsonication for 20 mins
  3. additionTo the degassed solution was added Tetrakis (triphenylphosphine) palladium (0.39 g) before it
  4. customwas degassed for a further 20 minutes
  5. customA reflux condenser was attached to the reaction vessel which
  6. customwas submerged into an oil bath
  7. temperaturewas cooled
  8. additiondiluted with EtOAc (50 ml)
  9. washwashed with water (20 ml) and saturated brine (20 ml)
  10. extractionOrganic extract
  11. customwas dried
  12. filtrationfiltered
  13. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-5b7ac1e641434fc986fef7f7636b33a3
Source dataset
uspto-grants-2006_05
Patent number
US07049313B2

Reaction notes

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