Potassium Phosphate, Tribasic → HCID 66817324, compound

HRID 1754922Notes

Reaction equation

HRID 1754922 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:25][CH2:24][C:11]2([N:15]=[C:14]([C:16]3[CH:21]=[CH:20][CH:19]=[C:18](Br)[CH:17]=3)[NH:13][C:12]2=[O:23])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH3:26][C:27]1[C:31](B(O)O)=[C:30]([CH3:35])[O:29][N:28]=1.[O-]P([O-])([O-])=O.[K+].[K+].[K+]>O1CCOCC1>[C:1]([O:5][C:6]([N:8]1[CH2:25][CH2:24][C:11]2([N:15]=[C:14]([C:16]3[CH:21]=[CH:20][CH:19]=[C:18]([C:31]4[C:27]([CH3:26])=[N:28][O:29][C:30]=4[CH3:35])[CH:17]=3)[NH:13][C:12]2=[O:23])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 62657Potassium Phosphate, TribasicHCID 27343463,5-Dimethylisoxazole-4-boronic acidHCID 66817048HCID 66817048, compound

Product 1

HCID 66817324HCID 66817324, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 2-(3-bromo-phenyl)-4-oxo-1,3,8-triaza-spiro[4.5]dec-1-ene-8-carboxylic acid tert-butyl ester (100 mg, 0.245 mmol), 3,5-dimethyl-isoxazole-4-boronic acid (51.8 mg, 0.367 mmol), tetrakis-(triphenylphosphine)palladium(0) (28 mg, 0.0245 mmol) and K3PO4 (104 mg, 0.490 mmol) in dioxane (1.2 mL) was heated with stirring at 100° C. for one hour in a nitrogen atmosphere. The reaction mixture was cooled, and then quenched with water and extracted with ethyl acetate (×3). The organic layers were combined and sequentially washed with water (×2) and saturated brine, and then dried over sodium sulfate and concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=2:1) to give 2-[3-(3,5-dimethyl-isoxazol-4-yl)-phenyl]-4-oxo-1,3,8-triaza-spiro[4.5]dec-1-ene-8-carboxylic acid tert-butyl ester as a pale yellow solid (88.3 mg, 85%).

Workup

  1. temperaturewas heated
  2. temperatureThe reaction mixture was cooled
  3. customquenched with water
  4. extractionextracted with ethyl acetate (×3)
  5. washsequentially washed with water (×2) and saturated brine
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customThe resulting residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=2:1)

Sources & evidence

ORD record
ord-b6d670d77dfa47d5b8cf7d57ad934efe
Source dataset
uspto-grants-2015_10
Patent number
US09169254B2

Reaction notes

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