Sodium Iodide → HCID 71557504, compound

HRID 509457Notes

Reaction equation

HRID 509457 reaction equation
[Na+].[I-].C[Si](Cl)(C)C.[F:8][C:9]1[CH:10]=[C:11]([C:16]2(O)[C:24]3[O:23][N:22]=[C:21]([C:25]4[CH:30]=[CH:29][C:28]([N:31]5[CH:35]=[C:34]([CH3:36])[N:33]=[CH:32]5)=[C:27]([O:37][CH3:38])[CH:26]=4)[C:20]=3[CH2:19][CH2:18][CH2:17]2)[CH:12]=[C:13]([F:15])[CH:14]=1>CC#N>[F:8][C:9]1[CH:10]=[C:11]([CH:16]2[C:24]3[O:23][N:22]=[C:21]([C:25]4[CH:30]=[CH:29][C:28]([N:31]5[CH:35]=[C:34]([CH3:36])[N:33]=[CH:32]5)=[C:27]([O:37][CH3:38])[CH:26]=4)[C:20]=3[CH2:19][CH2:18][CH2:17]2)[CH:12]=[C:13]([F:15])[CH:14]=1

Participants

5

Reactant 3

HCID 5238Sodium IodideHCID 6397ChlorotrimethylsilaneHCID 715575027-(3,5-difluorophenyl)-3-(3-Methoxy-4-(4-Methyl-1H-iMidazol-1-yl)phenyl)-4,5,6,7-tetrahydrobenzo[d]isoxazol-7-ol

Product 1

HCID 71557504HCID 71557504, compoundYield 66%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

To a suspension of NaI (1.54 g, 10.3 mmol) in CH3CN (20 mL) was added TMSCl (1.12 g, 10.27 mmol) and a solution of 7-(3,5-difluorophenyl)-3-(3-methoxy-4-(4-methyl-1H-imidazol-1-yl)phenyl)-4,5,6,7-tetrahydrobenzo[d]isoxazol-7-ol (691 mg, 1.6 mmol) in CH3CN (1.0 mL) The reaction mixture was stirred at 60° C. overnight, cooled, and partitioned between water and DCM. The organic phase was washed with 10% aq. Na2S2O3, water, and brine, dried over MgSO4 and concentrated. The crude product was purified by silica gel chromatography using 0-5% MeOH in DCM as solvent to afford 445 mg of the title product.

Workup

  1. temperaturecooled
  2. custompartitioned between water and DCM
  3. washThe organic phase was washed with 10% aq. Na2S2O3, water, and brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated
  6. customThe crude product was purified by silica gel chromatography

Sources & evidence

ORD record
ord-69be0a31478c4d8ea68ff0ce51116228
Source dataset
uspto-grants-2015_08
Patent number
US09096582B2

Reaction notes

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