Formic Acid → 2-(7-fluoro-1H-benzimidazol-1-yl)ethanol

HRID 419940노트

반응식

HRID 419940 반응식
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([N+:8]([O-])=O)[C:3]=1[NH:11][CH2:12][CH2:13][OH:14].[CH:15](O)=O>[Pd]>[F:1][C:2]1[C:3]2[N:11]([CH2:12][CH2:13][OH:14])[CH:15]=[N:8][C:4]=2[CH:5]=[CH:6][CH:7]=1

참가 물질

4

반응물 2

HCID 284Formic Acid2회HCID 114241932-[(2-Fluoro-6-nitrophenyl)amino]ethanol

생성물 1

HCID 113897452-(7-fluoro-1H-benzimidazol-1-yl)ethanol수율 64%

시약·촉매·용매 1

HCID 23938Palladium촉매

실험 절차

2-[(2-fluoro-6-nitrophenyl)amino]ethanol (18.3 g, 91.5 mmol) dissolved in 90 mL of formic acid is added to a suspension of Pd—C 10% (300 mg) in 10 ml of formic acid. The mixture is shaken in a Parr apparatus under atmospheric pressure of H2 overnight. The reaction mixture is filtered over Celite, the solvent is evaporated under vacuum and the resulting residue dissolved in NH3 2M in ethanol. This solution is stirred at room temperature for 1 h (to cleave the formic acid adduct). A precipitate forms. This mixture is evaporated to dryness and purified by column chromatography (SiO2, DCM/MeOH 10:1 to 5:1), giving the desired product as a white solid (10.5 g, 64%) TLC: DCM/MeOH 5:1, Rf=0.23.

후처리

  1. filtrationThe reaction mixture is filtered over Celite
  2. customthe solvent is evaporated under vacuum
  3. dissolutionthe resulting residue dissolved in NH3 2M in ethanol
  4. stirringThis solution is stirred at room temperature for 1 h (
  5. customThis mixture is evaporated to dryness
  6. custompurified by column chromatography (SiO2, DCM/MeOH 10:1 to 5:1)

출처 및 근거

ORD 기록
ord-647f868cf2364bc0882215abb42a4e38
출처 데이터셋
uspto-grants-2012_01
특허 번호
US08093402B2

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