Nitrogen → HCID 22139407, compound

HRID 1825778Notes

Reaction equation

HRID 1825778 reaction equation
Cl[C:2]1[O:3][C:4]([N:9]2[CH2:14][CH2:13][O:12][CH2:11][CH2:10]2)=[CH:5][C:6](=[O:8])[CH:7]=1.[F:15][C:16]1[C:29]2[C:28](=[O:30])[C:27]3[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=3)[S:21][C:20]=2[C:19](B2OC(C)(C)C(C)(C)O2)=[CH:18][CH:17]=1.C(=O)([O-])[O-].[K+].[K+].N#N>O1CCOCC1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[F:15][C:16]1[C:29]2[C:28](=[O:30])[C:27]3[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=3)[S:21][C:20]=2[C:19]([C:2]2[O:3][C:4]([N:9]3[CH2:14][CH2:13][O:12][CH2:11][CH2:10]3)=[CH:5][C:6](=[O:8])[CH:7]=2)=[CH:18][CH:17]=1

Participants

7

Reactant 4

HCID 947NitrogenHCID 11430Potassium CarbonateHCID 66052622-Chloro-6-morpholinopyran-4-oneHCID 22139435HCID 22139435, compound

Product 1

HCID 22139407HCID 22139407, compoundYield 4%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
90 °C

Procedure

2-Chloro-6-morpholin-4-yl-pyran-4-one (3) (100 mg, 0.46 mmol), 1-Fluoro-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-thioxanthen-9-one (12) (110 mg, 0.31 mmol), and ground potassium carbonate (63 mg, 0.62 mmol) were suspended in dioxane (5 ml) and degassed (sonication for 5 minutes then saturated with N2). Pd(PPh3)4 (18 mg, 0.016 mmol) was then added and the reaction mixture was then heated at 90° C. for 24 hours under a vigorous stirring and a N2 atmosphere. The solvent were removed in vacuo and the residue was then suspended in water (50 ml) and extracted with ethyl acetate (3×50 ml). The organics were combined, washed with saturated brine and dried over sodium sulphate. The solvent was removed in vacuo and the residue was purified by column chromatography (silica; ethyl acetate:ethanol; 9:1) to give the title compound as a white solid (5 mg, 4%). m/z (LC-MS, ESP): 410 (M++1).

Workup

  1. customdegassed (
  2. customsonication for 5 minutes
  3. customThe solvent were removed in vacuo
  4. extractionextracted with ethyl acetate (3×50 ml)
  5. washwashed with saturated brine
  6. dry with materialdried over sodium sulphate
  7. customThe solvent was removed in vacuo
  8. customthe residue was purified by column chromatography (silica; ethyl acetate:ethanol; 9:1)

Sources & evidence

ORD record
ord-5a2f17892bb74fdab3eaa8f30c771e05
Source dataset
uspto-grants-2006_05
Patent number
US07049313B2

Reaction notes

Loading…