1,2-Dimethoxyethane → Di-tert-butyl{3-[3-(bromomethyl)isoxazol-5-yl]pyridin-2-yl}imidodicarbonate

HRID 1960084Notes

Reaction equation

HRID 1960084 reaction equation
O[CH2:2][C:3]1[CH:7]=[C:6]([C:8]2[C:9]([N:14]([C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])=[N:10][CH:11]=[CH:12][CH:13]=2)[O:5][N:4]=1.C(N(CC)CC)C.COCCOC.P(Br)(Br)[Br:43]>O>[C:18]([O:17][C:15]([N:14]([C:9]1[C:8]([C:6]2[O:5][N:4]=[C:3]([CH2:2][Br:43])[CH:7]=2)=[CH:13][CH:12]=[CH:11][N:10]=1)[C:22]([O:24][C:25]([CH3:27])([CH3:26])[CH3:28])=[O:23])=[O:16])([CH3:20])([CH3:19])[CH3:21]

Participants

6

Reactant 4

HCID 80711,2-DimethoxyethaneHCID 8471TriethylamineHCID 24614Phosphorus tribromideHCID 57867426Di-tert-butyl{3-[3-(hydroxymethyl)isoxazol-5-yl]pyridin-2-yl}imidodicarbonate

Product 1

HCID 57867418Di-tert-butyl{3-[3-(bromomethyl)isoxazol-5-yl]pyridin-2-yl}imidodicarbonateYield 15.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a mixture of di-tert-butyl {3-[3-(hydroxymethyl)isoxazol-5-yl]pyridin-2-yl}imidodicarbonate (0.78 g, 2 mmol), triethylamine (1.95 mL, 14 mmol) and 1,2-dimethoxyethane (10 mL) was added phosphorus tribromide (0.37 mL, 4 mmol) dropwise at 0° C., which was stirred at room temperature for two hours, and then stirred at 50° C. for 30 minutes. The reaction mixture was cooled to 0° C., then water was added thereto and extracted with ethyl acetate, and the organic layer was washed with saturated sodium chloride water. After drying over anhydrous magnesium sulfate and filtering, the solvent was evaporated under a reduced pressure, the residue was purified by silica gel column chromatography, so as to obtain the title compound (0.14 g).

Workup

  1. stirringstirred at 50° C. for 30 minutes
  2. temperatureThe reaction mixture was cooled to 0° C.
  3. extractionextracted with ethyl acetate
  4. washthe organic layer was washed with saturated sodium chloride water
  5. dry with materialAfter drying over anhydrous magnesium sulfate
  6. filtrationfiltering
  7. customthe solvent was evaporated under a reduced pressure
  8. customthe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-7ee342434ebb42aa845837b456213a90
Source dataset
uspto-grants-2013_04
Patent number
US08410277B2

Reaction notes

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