4-(5-Iodoindazole-1-yl)-benzoic acid → (4-(5-iodo-1H-indazol-1-yl)phenyl)methanol

HRID 13176노트

반응식

HRID 13176 반응식
[I:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([C:11]1[CH:19]=[CH:18][C:14]([C:15](O)=[O:16])=[CH:13][CH:12]=1)[N:6]=[CH:5]2>C1COCC1>[I:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([C:11]1[CH:19]=[CH:18][C:14]([CH2:15][OH:16])=[CH:13][CH:12]=1)[N:6]=[CH:5]2

참가 물질

3

반응물 1

HCID 593397454-(5-Iodoindazole-1-yl)-benzoic acid

생성물 1

HCID 59339895(4-(5-iodo-1H-indazol-1-yl)phenyl)methanol수율 71.4%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

Crude 4-(5-iodo-1H-indazol-1-yl)benzoic acid (141c, 3.05 g, 8.4 mmol) was dissolved in THF (60 mL, dried over 4 Å MS) under argon atmosphere and cooled in an ice bath. Borane-THF complex (1M, 11 mL, 11 mmol) was added during 5 min. The ice bath was then removed and the mixture was allowed to reach r.t. and was finally heated at reflux for 40 min. The reaction mixture was then cooled to r.t. and sat. aqueous NH4Cl (25 mL) was added. After being diluted with EtOAc the reaction mixture was extracted trice with water and finally with brine and evaporated. The residue was subjected to chromatography (SiO2, 10-80% EtOAc in Heptane) to give (4-(5-iodo-1H-indazol-1-yl)phenyl)methanol (2.1 g, 71%).

후처리

  1. temperaturecooled in an ice bath
  2. additionBorane-THF complex (1M, 11 mL, 11 mmol) was added during 5 min
  3. customThe ice bath was then removed
  4. customto reach r.t.
  5. temperaturewas finally heated
  6. temperatureat reflux for 40 min
  7. additionsat. aqueous NH4Cl (25 mL) was added
  8. additionAfter being diluted with EtOAc the reaction mixture
  9. extractionwas extracted trice with water
  10. customfinally with brine and evaporated

출처 및 근거

ORD 기록
ord-e546c8b62cda4dbf9a7ab1ccf27aae67
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07728030B2

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