HCID 25132819, compound → HCID 25133157, compound

HRID 2262572Notes

Reaction equation

HRID 2262572 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:12]([C:13]3[N:14]=[CH:15][N:16]([C:18]4[N:23]=[CH:22][C:21]([C:24](=[O:26])[CH3:25])=[CH:20][CH:19]=4)[CH:17]=3)=[C:11]([C:27]([F:30])([F:29])[F:28])[O:10][N:9]=2)=[CH:4][CH:3]=1.[CH3:31][Mg]Br>C1COCC1.Cl>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[C:12]([C:13]3[N:14]=[CH:15][N:16]([C:18]4[N:23]=[CH:22][C:21]([C:24]([OH:26])([CH3:31])[CH3:25])=[CH:20][CH:19]=4)[CH:17]=3)=[C:11]([C:27]([F:28])([F:30])[F:29])[O:10][N:9]=2)=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 25132819HCID 25132819, compoundHCID 178418573HCID 178418573, compound

Product 1

HCID 25133157HCID 25133157, compoundYield 97%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 1-(6-{4-[3-(4-fluoro-phenyl)-5-trifluoromethyl-isoxazol-4-yl]-imidazol-1-yl}-pyridin-3-yl)-ethanone (50 mg, 0.12 mmol) in dry THF (2 mL) was added methylmagnesium bromide (3 M, 44 μL, 0.13 mmol) under nitrogen at room temperature and the resulting mixture stirred for 18 h. The mixture was then diluted with HCl (0.1 N) and then extracted with ethyl acetate. The combined organic extracts were then dried over sodium sulphate and evaporated. Purification by chromatography (SiO2, heptane:ethyl acetate=1:3 to 0:100) afforded the title compound (50.3 mg, 97%) which was obtained as a white solid. MS: m/e=433.3 [M+H]+.

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialThe combined organic extracts were then dried over sodium sulphate
  3. customevaporated
  4. customPurification by chromatography (SiO2, heptane:ethyl acetate=1:3 to 0:100)

Sources & evidence

ORD record
ord-29090966c0d1449bbdc2f8f16c823ddc
Source dataset
uspto-grants-2010_12
Patent number
US07851469B2

Reaction notes

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