Iodine → 3-(3-Fluoro-5-chloro-2-pyridyl)-4-iodo-5-difluoromethoxy-1-methyl-[1H]-pyrazole

HRID 1532579

Reaction equation

[F:1][C:2]1[C:3]([C:9]2[CH:13]=[C:12]([O:14][CH:15]([F:17])[F:16])[N:11]([CH3:18])[N:10]=2)=[N:4][CH:5]=[C:6]([Cl:8])[CH:7]=1.[I:19]I>C(Cl)Cl.C(OCC)C.N([O-])=O.[Ag+]>[F:1][C:2]1[C:3]([C:9]2[C:13]([I:19])=[C:12]([O:14][CH:15]([F:16])[F:17])[N:11]([CH3:18])[N:10]=2)=[N:4][CH:5]=[C:6]([Cl:8])[CH:7]=1

Participants

Conditions

Temperature: 22 °C

Procedure

3.0 g of 3-(3-fluoro-5-chloro-2-pyridyl)-5-difluoromethoxy-1-methyl-[1H]-pyrazole (Example H15) are dissolved in 30 ml of methylene chloride, and 1.83 g of silver(I) nitrite and 3.02 g of iodine are then added. The mixture is stirred overnight at 22° C. It is then diluted with diethyl ether and extracted successively with aqueous sodium metabisulfite solution and brine. After drying of the organic phase over sodium sulfate and filtration, the filtrate is concentrated in vacuo together with twice the amount of silica gel. After application of this silica gel to a flash column, the column is eluted with n-hexane/ethyl acetate (3/1). 3.97 g of the desired title compound are obtained as a beige solid of melting point 77-78° C. in this manner.

Workup

extractionextracted successively with aqueous sodium metabisulfite solution and brine
dry with materialAfter drying of the organic phase over sodium sulfate and filtration
concentrationthe filtrate is concentrated in vacuo together with twice the amount of silica gel
washAfter application of this silica gel to a flash column, the column is eluted with n-hexane/ethyl acetate (3/1)

Sources & evidence

ORD record: ord-30c05a42368142c3b41bdb27ae10dfb3
Source dataset: uspto-grants-2001_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06204221B1

Linked notes

Loading…