Pyridine → N-(2-Cyano-5-fluoro-4-iodo-6-methoxy-3-methylphenyl)-2,2-dimethylpropionamide

HRID 17320Notes

Reaction equation

N1C=CC=CC=1.[CH3:7][C:8]([CH3:27])([CH3:26])[C:9]([NH:11][C:12]1[C:20]([O:21][CH3:22])=[C:19]([F:23])[C:18]([I:24])=[C:17]([CH3:25])[C:13]=1[C:14]([NH2:16])=O)=[O:10].FC(F)(F)S(OS(C(F)(F)F)(=O)=O)(=O)=O>CN(C)C1C=CN=CC=1.C(OCC)(=O)C>[C:14]([C:13]1[C:17]([CH3:25])=[C:18]([I:24])[C:19]([F:23])=[C:20]([O:21][CH3:22])[C:12]=1[NH:11][C:9](=[O:10])[C:8]([CH3:26])([CH3:7])[CH3:27])#[N:16]

Participants

Conditions

Temperature: 0 °C

Procedure

4-Dimethylaminopyridine (149 mg, 1.22 mmol) was added to a pyridine (100 ml) suspension of 2-(2,2-dimethylpropionylamino)-4-fluoro-5-iodo-3-methoxy-6-methylbenzamide (I-68) (4.97 g, 1.22 mmol), and cooled at 0° C. Trifluoromethanesulfonic acid anhydride (6.17 ml, 36.5 mmol) was dropwise added to it, followed by stirring at room temperature for 1 hour, then ethyl acetate (400 ml) was put thereinto. The organic layer was washed with 1 N hydrochloric acid (300 ml×5), saturated brine (300 ml×2), then dried over anhydrous magnesium sulfate, concentrated under reduced pressure, the residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=5:1) to obtain the entitled compound (4.47 g, 94%) as a pale yellow solid.

Workup

washThe organic layer was washed with 1 N hydrochloric acid (300 ml×5), saturated brine (300 ml×2)
dry with materialdried over anhydrous magnesium sulfate
concentrationconcentrated under reduced pressure
customthe residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=5:1)

Sources & evidence

ORD record: ord-5b2dda62d2a0442d9551be8206b4575f
Source dataset: uspto-grants-2010_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07737166B2

Reaction notes

Loading…