Hydrochloric Acid → N-(3-Bromo-6-cyano-4-iodo-2-methoxy-5-methylphenyl)-2,2-dimethylpropionamide

HRID 17265

Reaction equation

HRID 17265 reaction equation
[Br:1][C:2]1[C:10]([I:11])=[C:9]([CH3:12])[C:5]([C:6]([NH2:8])=O)=[C:4]([NH:13][C:14](=[O:19])[C:15]([CH3:18])([CH3:17])[CH3:16])[C:3]=1[O:20][CH3:21].FC(F)(F)S(OS(C(F)(F)F)(=O)=O)(=O)=O.Cl>CN(C)C1C=CN=CC=1.N1C=CC=CC=1>[Br:1][C:2]1[C:3]([O:20][CH3:21])=[C:4]([NH:13][C:14](=[O:19])[C:15]([CH3:18])([CH3:16])[CH3:17])[C:5]([C:6]#[N:8])=[C:9]([CH3:12])[C:10]=1[I:11]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 67749Trifluoromethanesulfonic anhydrideHCID 866307964-Bromo-2-(2,2-dimethylpropionylamino)-5-iodo-3-methoxy-6-methylbenzamide

Product 1

HCID 86630795N-(3-Bromo-6-cyano-4-iodo-2-methoxy-5-methylphenyl)-2,2-dimethylpropionamide

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 1049PyridineSolvent

Conditions

Temperature
0 °C

Procedure

4-Dimethylaminopyridine (54.2 mg, 443 μmol) was added to a pyridine (40 ml) suspension of 4-bromo-2-(2,2-dimethylpropionylamino)-5-iodo-3-methoxy-6-methylbenzamide (I-5) (2.08 g, 4.43 mmol), followed by cooling at 0° C. To this, trifluoromethanesulfonic acid anhydride (2.25 ml, 13.3 mmol) was dropwise added, followed by stirring at room temperature for 2.5 hours, the reaction liquid was put into 1 N hydrochloric acid (200 ml), followed by extraction with ethyl acetate (200 ml×2). The organic layer was washed successively with 1 N hydrochloric acid (200 ml×2), saturated sodium bicarbonate water (50 ml), saturated brine (50 ml), then dried over anhydrous magnesium sulfate, concentrated under reduced pressure, the residue was purified twice by silica gel column chromatography (n-hexane:ethyl acetate=4:1) to obtain the entitled compound (1.86 g, quant.) as a pale yellow solid.

Workup

  1. customthe reaction liquid
  2. extractionfollowed by extraction with ethyl acetate (200 ml×2)
  3. washThe organic layer was washed successively with 1 N hydrochloric acid (200 ml×2), saturated sodium bicarbonate water (50 ml), saturated brine (50 ml)
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customthe residue was purified twice by silica gel column chromatography (n-hexane:ethyl acetate=4:1)
  7. customto obtain the entitled compound (1.86 g, quant.) as a pale yellow solid

Sources & evidence

ORD record
ord-e71df80c3cbd42818d8ba3dc3ac54a6e
Source dataset
uspto-grants-2010_06
Patent number
US07737166B2

Linked notes

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