N,N,N',N'-Tetramethylethylenediamine → 3-phenyl-4-(1-phenyl-1H-imidazol-4-yl)-5-trifluoromethyl-isoxazole

HRID 2262529Notes

Reaction equation

HRID 2262529 reaction equation
[NH:1]1[CH:5]=[C:4]([C:6]2[C:7]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)=[N:8][O:9][C:10]=2[C:11]([F:14])([F:13])[F:12])[N:3]=[CH:2]1.CN(CCN(C)C)C.[C:29]1(B(O)O)[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1>CO.O>[C:15]1([C:7]2[C:6]([C:4]3[N:3]=[CH:2][N:1]([C:29]4[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=4)[CH:5]=3)=[C:10]([C:11]([F:14])([F:12])[F:13])[O:9][N:8]=2)[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1

Participants

6

Reactant 3

HCID 8037N,N,N',N'-TetramethylethylenediamineHCID 66827Phenylboronic AcidHCID 178506308HCID 178506308, compound

Product 1

HCID 251304493-phenyl-4-(1-phenyl-1H-imidazol-4-yl)-5-trifluoromethyl-isoxazoleYield 42.2%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To a mixture of 4-(1H-imidazol-4-yl)-3-phenyl-5-trifluoromethyl-isoxazole (90 mg, 0.32 mmol) containing [Cu(OH).TMEDA]2Cl2 (14.95 mg, 0.032 mmol) in dry methanol (5 mL) was added phenylboronic acid (81.0 mg, 0.64 mmol) under an air atmosphere and the resulting mixture stirred at room temperature overnight. After this time, the resulting mixture was diluted with water and extracted with ethyl acetate. The organic extracts were then dried over sodium sulphate and evaporated. Purification by chromatography (SiO2, heptane:ethyl acetate=9:1 to 3:2) afforded the title compound (48 mg, 42%) which was obtained as a white solid. MS: m/e 356.3 [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 chromatography (SiO2, heptane:ethyl acetate=9:1 to 3:2)

Sources & evidence

ORD record
ord-9a567c089e8c4297a4f2252606447c27
Source dataset
uspto-grants-2010_12
Patent number
US07851469B2

Reaction notes

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