Sodium Iodide → N-{[6-iodo-1-(4-methoxybenzyl)-2-oxo-4-(trifluoromethyl)-1,4-dihydro-2H-3,1-benzoxazin-4-yl]methyl}-4-fluorobenzamide

HRID 1878027Notes

Reaction equation

HRID 1878027 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]2[N:10]([CH2:11][C:12]3[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][CH:13]=3)[C:9](=[O:20])[O:8][C:7]([CH2:25][NH:26][C:27](=[O:35])[C:28]3[CH:33]=[CH:32][C:31]([F:34])=[CH:30][CH:29]=3)([C:21]([F:24])([F:23])[F:22])[C:6]=2[CH:36]=1.[I-:37].[Na+].CNCCNC>O1CCOCC1.C(OCC)(=O)C.[Cu](I)I>[I:37][C:2]1[CH:3]=[CH:4][C:5]2[N:10]([CH2:11][C:12]3[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][CH:13]=3)[C:9](=[O:20])[O:8][C:7]([CH2:25][NH:26][C:27](=[O:35])[C:28]3[CH:33]=[CH:32][C:31]([F:34])=[CH:30][CH:29]=3)([C:21]([F:24])([F:23])[F:22])[C:6]=2[CH:36]=1

Participants

7

Reactant 3

HCID 5238Sodium IodideHCID 8070N,N'-DimethylethylenediamineHCID 44549804N-{[6-bromo-1-(4-methoxybenzyl)-2-oxo-4-(trifluoromethyl)-1,4-dihydro-2H-3,1-benzoxazin-4-yl]methyl}-4-fluorobenzamide

Product 1

HCID 44549927N-{[6-iodo-1-(4-methoxybenzyl)-2-oxo-4-(trifluoromethyl)-1,4-dihydro-2H-3,1-benzoxazin-4-yl]methyl}-4-fluorobenzamide

Reagents, catalysts & solvents 3

HCID 83717Copper iodideCatalystHCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
110 °C

Procedure

To a solution of N-{[6-bromo-1-(4-methoxybenzyl)-2-oxo-4-(trifluoromethyl)-1,4-dihydro-2H-3,1-benzoxazin-4-yl]methyl}-4-fluorobenzamide (1.18 g, 2.08 mmol), copper iodide (I) (79 mg, 0.416 mmol) and sodium iodide (624 mg, 4.16 mmol) in dioxane (4.2 mL), N,N′-dimethylethylene diamine (89 μL, 0.832 mmol) was added at room temperature. The reaction solution was stirred for 5 hours under heating at 110° C. The temperature of the solution was brought to room temperature, and the solution was diluted with ethyl acetate, which was washed sequentially with a saturated aqueous ammonium chloride solution and saturated brine and then dried over magnesium sulfate. After the drying agent was removed by filtration, the solvent was evaporated under reduced pressure. The resulting solid was washed with hexane and ethyl acetate, whereby the objective compound (995 mg, 78%) was obtained as a white solid.

Workup

  1. customwas brought to room temperature
  2. washwas washed sequentially with a saturated aqueous ammonium chloride solution and saturated brine
  3. dry with materialdried over magnesium sulfate
  4. customAfter the drying agent was removed by filtration
  5. customthe solvent was evaporated under reduced pressure
  6. washThe resulting solid was washed with hexane and ethyl acetate, whereby the objective compound (995 mg, 78%)
  7. customwas obtained as a white solid

Sources & evidence

ORD record
ord-e95de2c49f524960ab32b67f4bdd9b85
Source dataset
uspto-grants-2012_11
Patent number
US08314094B2

Reaction notes

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