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Tetrahydrofuran → N-[6-(4-Hydroxyphenyl)-1h-Indazol-3-Yl]butanamide

HRID 497609
ノート
印刷プレビュー

反応式

HRID 497609 の反応式
I[Si](C)(C)C.O1CCCC1.C1(C[O:18][C:19]2[CH:24]=[CH:23][C:22]([C:25]3[CH:33]=[C:32]4[C:28]([C:29]([NH:34][C:35](=[O:39])[CH2:36][CH2:37][CH3:38])=[N:30][NH:31]4)=[CH:27][CH:26]=3)=[CH:21][CH:20]=2)C=CC=CC=1>C(#N)C>[OH:18][C:19]1[CH:20]=[CH:21][C:22]([C:25]2[CH:33]=[C:32]3[C:28]([C:29]([NH:34][C:35](=[O:39])[CH2:36][CH2:37][CH3:38])=[N:30][NH:31]3)=[CH:27][CH:26]=2)=[CH:23][CH:24]=1
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 8028TetrahydrofuranHCID 85247Trimethylsilyl iodide2 回HCID 10452673N-(6-(4-(benzyloxy)phenyl)-1H-indazol-3-yl)butyramide

生成物 1

HCID 135458003N-[6-(4-Hydroxyphenyl)-1h-Indazol-3-Yl]butanamide

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

反応条件

温度
82 °C

実験手順

0.15 cm3 of iodotrimethylsilane and then 5 cm3 of tetrahydrofuran are added to 200 mg of N-[6-[4-(phenylmethoxy)phenyl]-1H-indazol-3-yl]butanamide, described previously, in 7.5 cm3 of acetonitrile, and the medium is heated at about 82° C. for 2 hours. 0.15 cm3 of iodotrimethylsilane is added and heating is continued for 17 hours. The reaction medium is then evaporated to dryness under reduced pressure (2 kPa; 40° C.). The residue is taken up in 75 cm3 of ethyl acetate, and this mixture is then washed with 2×50 cm3 of saturated aqueous sodium sulphate solution and with 50 cm3 of saturated sodium chloride solution. The organic phase is dried over magnesium sulphate, filtered and then evaporated under reduced pressure (2 kPa; 45° C.). The residue is purified by chromatography under an argon pressure of 50 kPa, on a column of silica gel (particle size 40-60 μm; diameter 1.5 cm), eluting with ethyl acetate and collecting 30 cm3 fractions. The fractions containing the expected product are combined and evaporated under reduced pressure (2 kPa; 50° C.). The residue is washed with 3×5 cm3 of diisopropyl ether. It is filtered off on a sinter funnel and, after drying (90 Pa; 40° C.), 100 mg of N-[6-(4-hydroxyphenyl)]-1H-indazol-3-yl]butanamide are thus obtained in the form of a white solid melting at about 235° C.

後処理

  1. temperatureheating
  2. customThe reaction medium is then evaporated to dryness under reduced pressure (2 kPa; 40° C.)
  3. washthis mixture is then washed with 2×50 cm3 of saturated aqueous sodium sulphate solution and with 50 cm3 of saturated sodium chloride solution
  4. dry with materialThe organic phase is dried over magnesium sulphate
  5. filtrationfiltered
  6. customevaporated under reduced pressure (2 kPa; 45° C.)
  7. customThe residue is purified by chromatography under an argon pressure of 50 kPa
  8. washon a column of silica gel (particle size 40-60 μm; diameter 1.5 cm), eluting with ethyl acetate
  9. customcollecting 30 cm3 fractions
  10. additionThe fractions containing the expected product
  11. customevaporated under reduced pressure (2 kPa; 50° C.)
  12. washThe residue is washed with 3×5 cm3 of diisopropyl ether
  13. filtrationIt is filtered off on a sinter funnel
  14. dry with materialafter drying (90 Pa; 40° C.), 100 mg of N-[6-(4-hydroxyphenyl)]-1H-indazol-3-yl]butanamide

出典と根拠

ORDレコード
ord-e0a7a4bab6bb4fb484349749fb3776a4
出典データセット
uspto-grants-2005_09
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US06949579B2

反応ノート

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