3-Fluoro-5-iodopicolinonitrile → Methyl 2-(6-cyano-5-fluoropyridin-3-yl)-6-fluorobenzoate

HRID 1374162노트

반응식

HRID 1374162 반응식
[F:1][C:2]1[C:3]([C:9]#[N:10])=[N:4][CH:5]=[C:6](I)[CH:7]=1.[F:11][C:12]1[C:13]([C:20]([O:22][CH3:23])=[O:21])=[C:14]([Zn]I)[CH:15]=[CH:16][CH:17]=1>C1COCC1>[C:9]([C:3]1[N:4]=[CH:5][C:6]([C:14]2[CH:15]=[CH:16][CH:17]=[C:12]([F:11])[C:13]=2[C:20]([O:22][CH3:23])=[O:21])=[CH:7][C:2]=1[F:1])#[N:10]

참가 물질

4

반응물 2

HCID 210758683-Fluoro-5-iodopicolinonitrileHCID 178498692HCID 178498692, 화합물

생성물 1

HCID 21075884Methyl 2-(6-cyano-5-fluoropyridin-3-yl)-6-fluorobenzoate

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

A solution of 3-fluoro-5-iodopyridine-2-carbonitrile (1.08 g, 3.87 mmol) in 10 mL of THF and palladium tetrakistriphenylphosphine (0.18 g, 0.16 mmol) was added to a solution of [3-fluoro-2-(methoxycarbonyl)phenyl](iodo)zinc (prepared from methyl 2-fluoro-6-iodobenzoate and Reike Zinc) in 20 mL of THF via cannula. The mixture was heated to reflux for one hour, cooled, and partitioned between ethyl acetate and water. The organic extract was washed with brine, dried over MgSO4, filtered and concentrated under vacuum. The residue was subjected to silica gel chromatography eluted with 0–20% ethyl acetate in hexanes to provide methyl 2-(6-cyano-5-fluoropyridin-3-yl)-6-fluorobenzoate that gave proton NMR spectra consistent with theory.

후처리

  1. temperatureThe mixture was heated
  2. temperatureto reflux for one hour
  3. temperaturecooled
  4. custompartitioned between ethyl acetate and water
  5. extractionThe organic extract
  6. washwas washed with brine
  7. dry with materialdried over MgSO4
  8. filtrationfiltered
  9. concentrationconcentrated under vacuum
  10. washeluted with 0–20% ethyl acetate in hexanes

출처 및 근거

ORD 기록
ord-bc86ad7b1b81453584731b89221b3090
출처 데이터셋
uspto-grants-2007_01
특허 번호
US07163951B2

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