Potassium Carbonate → HCID 22139398, compound

HRID 1825787Notes

Reaction equation

HRID 1825787 reaction equation
CC1(C)C(C)(C)OB([C:9]2[C:22]3[CH2:21][C:20]4[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=4)[S:14][C:13]=3[C:12]([O:23]C(=O)OC(C)(C)C)=[CH:11][CH:10]=2)O1.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>[OH:23][C:12]1[C:13]2[S:14][C:15]3[C:20](=[CH:19][CH:18]=[CH:17][CH:16]=3)[CH2:21][C:22]=2[C:9]([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:11]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 66052622-Chloro-6-morpholinopyran-4-oneHCID 67524621HCID 67524621, compound

Product 1

HCID 22139398HCID 22139398, compoundYield 18.9%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
90 °C

Procedure

Carbonic acid tert-butyl ester 1-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-9H-thioxanthen-4-yl ester (3.00 g, 6.81 mmol), 2-chloro-6-morpholin-4-yl-pyran-4-one (1.22 g, 5.67 mmol) and potassium carbonate (2.07 g, 14.98 mmol) were suspended in anhydrous dioxane (6 ml) under nitrogen atmosphere. The solution was degassed for 15 minutes. To the solution tetrakis(triphenylphosphino) palladium (291 mg, 5% eq.) was added. The mixture was degassed for a further 5 minutes. The reaction was heated at 90° C. under nitrogen atmosphere for 24 hours. The solvent was evaporated in vacuo and the crude mixture was purified by column chromatography (9:1, ethyl acetate/ethanol), to yield the title compound (421 mg, 16%) as a light yellow amorphous solid. 1H NMR (300 MHz, DMSO-d6): δH=3.33 (4H, t), 3.67 (4H, t), 3.88 (2H, s), 5.45 (1H, d), 6.05 (1H, d), 6.87 (1H, d), 7.24–7.65 (5H, m), 10.62 (1H, bs); m/z (LC-MS, ESP), RT=3.96 min, (M++1)=394.

Workup

  1. customThe solution was degassed for 15 minutes
  2. additionTo the solution tetrakis(triphenylphosphino) palladium (291 mg, 5% eq.) was added
  3. customThe mixture was degassed for a further 5 minutes
  4. customThe solvent was evaporated in vacuo
  5. customthe crude mixture was purified by column chromatography (9:1, ethyl acetate/ethanol)

Sources & evidence

ORD record
ord-e3a02019fa214321886f8d3a628d4670
Source dataset
uspto-grants-2006_05
Patent number
US07049313B2

Reaction notes

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