Nitrogen → KU-55933

HRID 1825774Notes

Reaction equation

HRID 1825774 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:28]2[S:27][C:26]3[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=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:25]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:26]2[S:27][C:28]3[C:19](=[CH:18][CH:17]=[CH:16][CH:15]=3)[S:20][C:21]=2[CH:22]=[CH:23][CH:24]=1

Participants

7

Reactant 4

HCID 947NitrogenHCID 11430Potassium CarbonateHCID 2734382Thianthrene-1-boronic acidHCID 66052622-Chloro-6-morpholinopyran-4-one

Product 1

HCID 5278396KU-55933Yield 4.4%

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) (863 mg, 4 mmol), thianthrene-1-boronic acid (1.145 g, 4.4 mmol), and ground potassium carbonate (1.105 g, 8 mmol) were suspended in dioxane (10 ml) and degassed (sonication for 5 minutes then saturated with N2). Pd(PPh3)4 (231 mg, 0.2 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 was removed in vacuo and the residue was then suspended in water 50 ml) and extracted with ethyl acetate (3×100 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 (70 mg, 4%). 1H-NMR (300 MHz, DMSO-d6): δH=3.44 (4H, t, J 5 Hz); 3.76 (4H, t, J 5 Hz); 5.57 (1H, d, J 2 Hz); 6.30 (1H, d, J 2 Hz); 7.43 (2H, m); 7.53 (1H, t, 8 Hz); 7.66 (3H, m); 8.49 (1H, dd, J land 8 Hz). m/z (LC-MS, ESP): 396 (M++1).

Workup

  1. customdegassed (
  2. customsonication for 5 minutes
  3. customThe solvent was removed in vacuo
  4. extractionextracted with ethyl acetate (3×100 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-8752acd453ce4f6ca0604f497ce09ffc
Source dataset
uspto-grants-2006_05
Patent number
US07049313B2

Reaction notes

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