Nitrogen → HCID 16203592, compound

HRID 1765039Notes

Reaction equation

HRID 1765039 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:20]=[C:21](B(O)O)[CH:22]=[CH:23][CH:24]=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:20]=[CH:21][CH:22]=[C:23]([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:24]=1

Participants

7

Reactant 4

HCID 947NitrogenHCID 11430Potassium CarbonateHCID 27347143-(Methoxycarbonyl)benzeneboronic acidHCID 66052622-Chloro-6-morpholinopyran-4-one

Product 1

HCID 16203592HCID 16203592, compoundYield 46.5%

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 (7.98 g, 37 mmol), (3-methoxycarbonylphenyl) boronic acid (8.01 g, 44.5 mmol), and ground potassium carbonate (11.23 g, 81.40 mmol) were suspended in dioxane (50 ml) and degassed (sonication for 5 min then saturated with N2). Pd(PPh3)4 (2.13 g, 1.85 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 vaccuo and the residue was purified by column chromatography (silica; dichloromethane:methanol; 9:1) to give the title compound as a white solid (5.42 g, 46%). 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 vaccuo
  8. customthe residue was purified by column chromatography (silica; dichloromethane:methanol; 9:1)

Sources & evidence

ORD record
ord-9d8e7922692d4b9db6b146869bc0c1bd
Source dataset
uspto-grants-2007_06
Patent number
US07226918B2

Reaction notes

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