N-Iodosuccinimide → 3-[1-(2,6-Dichloro-3-fluorophenyl)ethoxy]-5-iodopyridin-2-amine

HRID 1627515노트

반응식

HRID 1627515 반응식
[Cl:1][C:2]1[C:7]([F:8])=[CH:6][CH:5]=[C:4]([Cl:9])[C:3]=1[CH:10]([O:12][C:13]1[C:14]([NH2:19])=[N:15][CH:16]=[CH:17][CH:18]=1)[CH3:11].[I:20]N1C(=O)CCC1=O>C(#N)C.C(O)(=O)C>[I:20][C:17]1[CH:18]=[C:13]([O:12][CH:10]([C:3]2[C:4]([Cl:9])=[CH:5][CH:6]=[C:7]([F:8])[C:2]=2[Cl:1])[CH3:11])[C:14]([NH2:19])=[N:15][CH:16]=1

참가 물질

5

반응물 2

HCID 120273N-IodosuccinimideHCID 211113963-(1-(2,6-Dichloro-3-fluorophenyl)ethoxy)pyridin-2-amine

생성물 1

HCID 211113953-[1-(2,6-Dichloro-3-fluorophenyl)ethoxy]-5-iodopyridin-2-amine수율 50.1%

시약·촉매·용매 2

HCID 176Acetic Acid용매HCID 6342Acetonitrile용매

실험 절차

To a solution of 3-[1-(2,6-Dichloro-3-fluoro-phenyl)ethoxy]-pyridin-2-ylamine (10.0 g, 33.2 mmol) in acetonitrile (600 mL) and acetic acid (120 mL) was added N-iodosuccinimide (11.2 g, 49.8 mmol). The mixture was stirred at room temperature for 4 h and the reaction was quenched with Na2S2O5 solution. After evaporation, the residue was partitioned between ethyl acetate and water. The organic layer was washed with 2N NaOH solution, brine, and dried over Na2SO4. The crude product was purified on a silica gel column to provide 5-iodo-3-[1-(2,6-dichloro-3-fluoro-phenyl)-ethoxy]-pyridin-2-ylamine (7.1 g, 50% yield). MS m/z 427 [M+1]. 1H NMR (400 MHz, DMSO-D6) δ ppm 1.74 (d, J=6.57 Hz, 3H) 5.91-5.99 (m, 3H) 6.82 (d, J=1.26 Hz, 1H) 7.46 (t, J=8.72 Hz, 1H) 7.56 (dd, J=8.97, 4.93 Hz, 1H) 7.62 (d, J=1.52 Hz, 1H).

후처리

  1. customthe reaction was quenched with Na2S2O5 solution
  2. customAfter evaporation
  3. customthe residue was partitioned between ethyl acetate and water
  4. washThe organic layer was washed with 2N NaOH solution, brine
  5. dry with materialdried over Na2SO4
  6. customThe crude product was purified on a silica gel column

출처 및 근거

ORD 기록
ord-344eed5b81584d9882d221aacf970343
출처 데이터셋
uspto-grants-2014_07
특허 번호
US08785632B2

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