Trimethylsilyl iodide → N-(6-(3-hydroxyphenyl)-1H-indazol-3-yl)butyramide

HRID 497658노트

반응식

HRID 497658 반응식
C[Si](I)(C)C.C1(C[O:13][C:14]2[CH:15]=[C:16]([C:20]3[CH:28]=[C:27]4[C:23]([C:24]([NH:29][C:30](=[O:34])[CH2:31][CH2:32][CH3:33])=[N:25][NH:26]4)=[CH:22][CH:21]=3)[CH:17]=[CH:18][CH:19]=2)C=CC=CC=1>CO>[OH:13][C:14]1[CH:15]=[C:16]([C:20]2[CH:28]=[C:27]3[C:23]([C:24]([NH:29][C:30](=[O:34])[CH2:31][CH2:32][CH3:33])=[N:25][NH:26]3)=[CH:22][CH:21]=2)[CH:17]=[CH:18][CH:19]=1

참가 물질

4

반응물 2

HCID 85247Trimethylsilyl iodideHCID 22319688N-[6-[3-(phenylmethoxy)phenyl]-1H-indazol-3-yl]butanamide

생성물 1

HCID 22319573N-(6-(3-hydroxyphenyl)-1H-indazol-3-yl)butyramide수율 58.7%

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

10 cm3 of trimethylsilyl iodide are added to 0.4 g of N-[6-[3-(phenylmethoxy)phenyl]-1H-indazol-3-yl]butanamide, described previously, and the mixture is refluxed for 3 hours. 50 cm3 of methanol are then added and refluxing is continued for 15 minutes. The reaction medium is concentrated to dryness under reduced pressure (2 kPa; 50° C.), 50 cm3 of ethyl acetate are added and the organic phase is washed with 3×50 cm3 of 10% sodium thiosulphate solution. The organic phase is separated out after settling of the phases has taken place, dried over magnesium sulphate, filtered and concentrated to dryness under reduced pressure (2 kPa; 50° C.). The crude product obtained is purified by chromatography under an argon pressure of 50 kPa, on a column of silica gel (particle size 40-60 μm; diameter 2.5 cm), eluting with a cyclohexane/ethyl acetate mixture (50/50 by volume). The fractions containing the expected product are combined and evaporated under reduced pressure (2 kPa; 50° C.); 0.18 g of N-[6-(3-hydroxyphenyl)-1H-indazol-3-yl]butanamide is obtained in the form of a grey powder melting at 188° C.

후처리

  1. temperaturethe mixture is refluxed for 3 hours
  2. temperaturerefluxing
  3. concentrationThe reaction medium is concentrated to dryness under reduced pressure (2 kPa; 50° C.), 50 cm3 of ethyl acetate
  4. additionare added
  5. washthe organic phase is washed with 3×50 cm3 of 10% sodium thiosulphate solution
  6. customThe organic phase is separated out
  7. dry with materialdried over magnesium sulphate
  8. filtrationfiltered
  9. concentrationconcentrated to dryness under reduced pressure (2 kPa; 50° C.)
  10. customThe crude product obtained
  11. customis purified by chromatography under an argon pressure of 50 kPa
  12. washon a column of silica gel (particle size 40-60 μm; diameter 2.5 cm), eluting with a cyclohexane/ethyl acetate mixture (50/50 by volume)
  13. additionThe fractions containing the expected product
  14. customevaporated under reduced pressure (2 kPa; 50° C.)

출처 및 근거

ORD 기록
ord-1d51498238eb419a94f0cded6bc0c364
출처 데이터셋
uspto-grants-2005_09
특허 번호
US06949579B2

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