Nitrogen → HCID 16203593, compound

HRID 1765041Notes

Reaction equation

HRID 1765041 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.[CH3:15][O:16][C:17]([C:19]1[CH:24]=[CH:23][C:22](B(O)O)=[CH:21][CH:20]=1)=[O:18].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>[CH3:15][O:16][C:17](=[O:18])[C:19]1[CH:24]=[CH:23][C:22]([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:21][CH:20]=1

Participants

7

Reactant 4

HCID 947NitrogenHCID 11430Potassium CarbonateHCID 27343694-Methoxycarbonylphenylboronic acidHCID 66052622-Chloro-6-morpholinopyran-4-one

Product 1

HCID 16203593HCID 16203593, compoundYield 63.3%

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 (4.01 g, 18.60 mmol), (4-methoxycarbonylphenyl)boronic acid (4.01 g, 22.32 mmol), and ground potassium carbonate (5.64 g, 40.92 mmol) were suspended in dioxane (20 ml) and degassed (sonication for 5 min then saturated with N2). Pd(PPh3)4 (0.5 g, 0.4 mmol) was then added and the reaction mixture was then heated at 90° C. for 24 hrs 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 (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; dichloromethane:methanol; 9:1) to give the title compound as a white solid 3.71 g, 63%). m/z (LC-MS, ESP): 316 (M++1).

Workup

  1. customdegassed (
  2. customsonication for 5 min
  3. customThe solvent were removed in vacuo
  4. extractionextracted with ethyl acetate (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; dichloromethane:methanol; 9:1)

Sources & evidence

ORD record
ord-fb9c4f784173450e94c9a81cd9de30a0
Source dataset
uspto-grants-2007_06
Patent number
US07226918B2

Reaction notes

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