Nitrogen → HCID 22139439, compound

HRID 1825776Notes

Reaction equation

HRID 1825776 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.[C:15]1(B(O)O)[C:23]2[C:22]3[CH:24]=[CH:25][CH:26]=[CH:27][C:21]=3[S:20][C:19]=2[CH:18]=[CH:17][CH:16]=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>[C:15]1([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)[C:23]2[C:22]3[CH:24]=[CH:25][CH:26]=[CH:27][C:21]=3[S:20][C:19]=2[CH:18]=[CH:17][CH:16]=1

Participants

7

Reactant 4

HCID 947NitrogenHCID 11430Potassium CarbonateHCID 66052622-Chloro-6-morpholinopyran-4-oneHCID 17750866HCID 17750866, compound

Product 1

HCID 22139439HCID 22139439, compoundYield 6.4%

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)(740 mg, 3.43 mmol), dibenzothiophene-1-boronic acid (860 mg, 3.77 mmol), and ground potassium carbonate (964 mg, 6.86 mmol) were suspended in dioxane (10 ml) and degassed (sonication for 5 minutes then saturated with N2). Pd(PPh3)4 (200 mg, 0.17 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 (80 mg, 6%). 1H-NMR (300 MHz, DMSO-d6): δH=3.49 (4H, t, J 5 Hz); 3.76 (4H, t, J 5 Hz); 5.53 (1H, d, J 2 Hz); 6.63 (1H, d, J 2 Hz); 7.59 (2H, m); 7.69 (1H, t, J 8 Hz); 7.96 (1H, dd, J 1 and 7.5 Hz); 8.11 (1H, m); 8.47 (1H, m); 8.57 (1H, dd, J 1 and 8 Hz). m/z (LC-MS, ESP): 364 (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-e84f704ac785435d93f9d7bea25cf6b1
Source dataset
uspto-grants-2006_05
Patent number
US07049313B2

Reaction notes

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