HCID 25131428, compound → HCID 25131770, compound

HRID 2262559Notes

Reaction equation

HRID 2262559 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[CH: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[CH: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:30])([F:28])[F:29])[O:10][N:9]=2)=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 25131428HCID 25131428, compoundHCID 178418573HCID 178418573, compound2×

Product 1

HCID 25131770HCID 25131770, compoundYield 48.3%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 1-(4-{4-[3-(4-fluoro-phenyl)-5-trifluoromethyl-isoxazol-4-yl]-imidazol-1-yl}-phenyl)-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, after which time methylmagnesium bromide (3 M, 40 μL, 0.12 mmol) was added and the resulting mixture stirred for 19 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 (25 mg, 48%) which was obtained as a white solid. MS: m/e=432.3 [M+H]+.

Workup

  1. stirringthe resulting mixture stirred for 19 h
  2. extractionextracted with ethyl acetate
  3. dry with materialThe combined organic extracts were then dried over sodium sulphate
  4. customevaporated
  5. customPurification by chromatography (SiO2, heptane:ethyl acetate=1:3 to 0:100)

Sources & evidence

ORD record
ord-70a60ff793404d1fbbdd837cf973831c
Source dataset
uspto-grants-2010_12
Patent number
US07851469B2

Reaction notes

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