Potassium Carbonate → 6-(4-{[Tert-butyl(dimethyl)silyl]oxy}butyl)-7-propyl-3-(trifluoromethyl)-1,2-benzisoxazole

HRID 1245338Notes

Reaction equation

HRID 1245338 reaction equation
[CH2:1]([O:5][Si:6]([C:9]([CH3:12])([CH3:11])[CH3:10])([CH3:8])[CH3:7])[CH2:2][CH:3]=[CH2:4].B1C2CCCC1CCC2.FC(F)(F)S(O[C:28]1[CH:40]=[CH:39][C:31]2[C:32]([C:35]([F:38])([F:37])[F:36])=[N:33][O:34][C:30]=2[C:29]=1[CH2:41][CH2:42][CH3:43])(=O)=O.C([O-])([O-])=O.[K+].[K+]>C1COCC1.CN(C=O)C.[Pd]>[Si:6]([O:5][CH2:1][CH2:2][CH2:3][CH2:4][C:28]1[CH:40]=[CH:39][C:31]2[C:32]([C:35]([F:37])([F:38])[F:36])=[N:33][O:34][C:30]=2[C:29]=1[CH2:41][CH2:42][CH3:43])([C:9]([CH3:12])([CH3:11])[CH3:10])([CH3:7])[CH3:8]

Participants

8

Reactant 4

HCID 11430Potassium CarbonateHCID 789669-Borabicyclo(3.3.1)nonaneHCID 10008065(But-3-enyloxy)(tert-butyl)dimethylsilaneHCID 219109917-Propyl-3-(trifluoromethyl)-1,2-benzisoxazol-6-yl trifluoromethanesulfonate

Product 1

HCID 219110176-(4-{[Tert-butyl(dimethyl)silyl]oxy}butyl)-7-propyl-3-(trifluoromethyl)-1,2-benzisoxazole

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (but-3-enyloxy)(tert-butyl)dimethylsilane, from this Example step 2, (148 mg, 0.79 mmol) in dry THF (0.25 mL) was added 9-BBN (0.5M 1.75 mL, 0.88 mmol) at 0° C. under N2. The mixture was stirred for 5 hours, then added to a mixture of 7-propyl-3-(trifluoromethyl)-1,2-benzisoxazol-6-yl trifluoromethanesulfonate, as prepared in this Example step 1, (300 mg, 0.79 mmol), K2CO3 (220 mg, 1.59 mmol), and dichlorobis(triphenylphosphene) palladium (32.5 mg, 0.039 mmol) in DMF (3 mL) under N2 in a sealed tube. The mixture was stirred overnight at 55° C. The reaction mixture was partitioned between ethyl acetate and water. Combined organic extracts were washed with water twice and brine and then dried over Na2SO4. The solvent was evaporated in vacuo. The residue was purified by chromatography on silica gel using ethyl acetate and hexane (1:30) to give the title compound.

Workup

  1. customat 0° C.
  2. stirringThe mixture was stirred overnight at 55° C
  3. customThe reaction mixture was partitioned between ethyl acetate and water
  4. washCombined organic extracts were washed with water twice
  5. dry with materialbrine and then dried over Na2SO4
  6. customThe solvent was evaporated in vacuo
  7. customThe residue was purified by chromatography on silica gel

Sources & evidence

ORD record
ord-0a561ba0647e46139d81dab0bac9f51b
Source dataset
uspto-grants-2006_10
Patent number
US07125865B2

Reaction notes

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