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

HRID 1532579

반응식

HRID 1532579 반응식
[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

참가 물질

6

반응물 2

HCID 807IodineHCID 217121323-(3-fluoro-5chloro-2-pyridyl)-5-difluoromethoxy-1-methyl-[1H]-pyrazole

생성물 1

HCID 220135793-(3-Fluoro-5-chloro-2-pyridyl)-4-iodo-5-difluoromethoxy-1-methyl-[1H]-pyrazole수율 91%

시약·촉매·용매 3

HCID 160904Silver nitrite촉매HCID 3283Diethyl Ether용매HCID 6344Dichloromethane용매

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온도
22 °C

실험 절차

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.

후처리

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

출처 및 근거

ORD 기록
ord-30c05a42368142c3b41bdb27ae10dfb3
출처 데이터셋
uspto-grants-2001_03
특허 번호
US06204221B1

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