Ammonia → HCID 23725206, compound

HRID 2219303Notes

Reaction equation

HRID 2219303 reaction equation
[NH:1]1[CH:5]=[C:4]([C:6]2[C:7]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)=[N:8][O:9][C:10]=2[CH3:11])[N:3]=[CH:2]1.CN(CCN(C)C)C.[F:26][C:27]1[CH:32]=[CH:31][C:30](B(O)O)=[CH:29][CH:28]=1.N>CO.O>[F:26][C:27]1[CH:32]=[CH:31][C:30]([N:1]2[CH:5]=[C:4]([C:6]3[C:7]([C:12]4[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=4)=[N:8][O:9][C:10]=3[CH3:11])[N:3]=[CH:2]2)=[CH:29][CH:28]=1

Participants

7

Reactant 4

HCID 222AmmoniaHCID 8037N,N,N',N'-TetramethylethylenediamineHCID 2856454-Fluorophenylboronic acidHCID 178434980HCID 178434980, compound

Product 1

HCID 23725206HCID 23725206, compoundYield 21.3%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To a mixture of 4-(1H-imidazol-4-yl)-5-methyl-3-phenyl-isoxazole (112.6 mg, 0.5 mmol) containing [Cu(OH).TMEDA]2Cl2 (23.2 mg, 0.05 mmol) in dry methanol (5 mL) was added 4-fluorophenylboronic acid (140 mg, 1.0 mmol) under an air atmosphere and the resulting mixture stirred at room temperature overnight. After this time, concentrated ammonia solution (2 mL) was added and then the resulting mixture was diluted with water (20 mL) and extracted with ethyl acetate. The organic extracts were then dried over sodium sulphate and evaporated. Purification by preparative HPLC on reversed phase eluting with an acetonitrile/water [0.1% aq NH3 (25%)] gradient afforded the title compound (34 mg, 21%) which was obtained as a white solid. MS (ESI): m/e=320.0 [M+H]+.

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialThe organic extracts were then dried over sodium sulphate
  3. customevaporated
  4. customPurification by preparative HPLC on reversed phase
  5. washeluting with an acetonitrile/water [0.1% aq NH3 (25%)] gradient

Sources & evidence

ORD record
ord-34dc55a5f7aa4729a54080d11266cceb
Source dataset
uspto-grants-2008_08
Patent number
US07414061B2

Reaction notes

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