Hydrochloric Acid → 6-methyl-5-(6-(trifluoromethyl)-1H-indazol-4-yl)picolinic acid

HRID 58040노트

반응식

HRID 58040 반응식
[CH3:1][C:2]1[N:7]=C(C#N)[CH:5]=[CH:4][C:3]=1[C:10]1[CH:18]=[C:17]([C:19]([F:22])([F:21])[F:20])[CH:16]=[C:15]2[C:11]=1[CH:12]=[N:13][NH:14]2.[OH-:23].[Na+].Cl.[CH3:26][CH2:27][OH:28]>>[CH3:1][C:2]1[N:7]=[C:26]([C:27]([OH:23])=[O:28])[CH:5]=[CH:4][C:3]=1[C:10]1[CH:18]=[C:17]([C:19]([F:22])([F:21])[F:20])[CH:16]=[C:15]2[C:11]=1[CH:12]=[N:13][NH:14]2

참가 물질

5

반응물 4

HCID 313Hydrochloric AcidHCID 702EthanolHCID 14798Sodium HydroxideHCID 897829316-methyl-5-(6-(trifluoromethyl)-1H-indazol-4-yl)picolinonitrile

생성물 1

HCID 897833556-methyl-5-(6-(trifluoromethyl)-1H-indazol-4-yl)picolinic acid수율 89%

실험 절차

To 6-methyl-5-(6-(trifluoromethyl)-1H-indazol-4-yl)picolinonitrile (1.7 g, 5.62 mmol) in EtOH (20 mL) was added sodium hydroxide (14.06 mL, 28.1 mmol) and the resulting mixture was stirred for 16 hours at reflux. The mixture was subsequently cooled to room temperature and acidified with concentrated HCl. Volatiles were evaporated and the residue purified by CombiFlash® chromatography (5-40% MeOH in DCM over 120 minutes). The product-containing fractions were combined and concentrated in vacuo to give the title compound as a white solid (1.6 g, 89%). ESI-MS m/z [M+H]+ calc'd for C15H10F3N3O2, 322.1. found 322.06.

후처리

  1. temperatureat reflux
  2. customVolatiles were evaporated
  3. customthe residue purified by CombiFlash® chromatography (5-40% MeOH in DCM over 120 minutes)
  4. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-67116a1f1f614286a64f0da071cfc36a
출처 데이터셋
uspto-grants-2016_09
특허 번호
US09434743B2

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