HCID 89545174, compound → HCID 71557502, compound

HRID 509456Notes

Reaction equation

HRID 509456 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:15]2[C:19]3[CH2:20][CH2:21][CH2:22][C:23](=[O:24])[C:18]=3[O:17][N:16]=2)[CH:6]=[CH:7][C:8]=1[N:9]1[CH:13]=[C:12]([CH3:14])[N:11]=[CH:10]1.[F:25][C:26]1[CH:27]=[C:28]([Mg]Br)[CH:29]=[C:30]([F:32])[CH:31]=1>C1COCC1>[F:25][C:26]1[CH:27]=[C:28]([C:23]2([OH:24])[C:18]3[O:17][N:16]=[C:15]([C:5]4[CH:6]=[CH:7][C:8]([N:9]5[CH:13]=[C:12]([CH3:14])[N:11]=[CH:10]5)=[C:3]([O:2][CH3:1])[CH:4]=4)[C:19]=3[CH2:20][CH2:21][CH2:22]2)[CH:29]=[C:30]([F:32])[CH:31]=1

Participants

4

Reactant 2

HCID 89545174HCID 89545174, compoundHCID 178505930HCID 178505930, compound2×

Product 1

HCID 71557502HCID 71557502, compoundYield 69.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of 3-(3-methoxy-4-(4-methyl-1H-imidazol-1-yl)phenyl)-5,6-dihydrobenzo[d]isoxazol-7(4H)-one (880 mg, 2.72 mmol) in THF (15 ml) at 0° C., was added slowly (3,5-difluorophenyl)magnesium bromide (6.54 mL of 0.5 M solution in THF, 3.27 mmol) and the reaction was stirred for 3 hr. Additional amount of (3,5-difluorophenyl)magnesium bromide (6.0 mL of 0.5 M solution in THF, 3.0 mmol) was added and stirring was continued at 0° C. for 2 hr. The reaction mixture was quenched with water, extracted with ethyl acetate, and the organic phase was washed with water and brine, dried over sodium sulfate and concentrated. The crude product was purified by silica gel chromatography using 0-6% MeOH in DCM as solvent to afford the 828 mg of the title product.

Workup

  1. stirringstirring
  2. waitwas continued at 0° C. for 2 hr
  3. customThe reaction mixture was quenched with water
  4. extractionextracted with ethyl acetate
  5. washthe organic phase was washed with water and brine
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated
  8. customThe crude product was purified by silica gel chromatography

Sources & evidence

ORD record
ord-cc0b1123758c41c995a77207c7bf600a
Source dataset
uspto-grants-2015_08
Patent number
US09096582B2

Reaction notes

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