Hydrochloric Acid → 1-Cyclohexyl-3-ethyl-6-fluoro-1H-indazole

HRID 612844

반응식

HRID 612844 반응식
F[C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C:9](=O)[CH2:10][CH3:11].C([O-])(=O)C.[Na+].S(O)(=O)(=O)C.[CH:23]1([NH:29][NH2:30])[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]1.Cl>C1(C)C=CC=CC=1>[CH:23]1([N:29]2[C:2]3[C:3](=[CH:4][CH:5]=[C:6]([F:8])[CH:7]=3)[C:9]([CH2:10][CH3:11])=[N:30]2)[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]1

참가 물질

6

반응물 4

HCID 313Hydrochloric AcidHCID 1235862',4'-DifluoropropiophenoneHCID 517045Sodium AcetateHCID 22009940Cyclohexylhydrazine mesylate

생성물 1

HCID 98596991-Cyclohexyl-3-ethyl-6-fluoro-1H-indazole수율 98%

시약·촉매·용매 1

HCID 1140Toluene용매

실험 절차

To a solution of 1-(2,4-difluoro-phenyl)-propan-1-one (21.29 g, 125.1 mmol) in toluene (120 mL) was added sodium acetate (26.75 g, 326.1 mmol) and cyclohexylhydrazine mesylate (34.0 g, 163 mmol). The reaction mixture was heated to reflux in a Dean-Stark apparatus for 12 hours. The reaction was cooled to room temperature and poured into 1 N hydrochloric acid (100 mL). The toluene layer was separated and washed with water (75 mL) and brine (75 mL). The organic layer was dried over magnesium sulfate, filtered, and concentrated to yield 30.07 g of 1-cyclohexyl-3-ethyl-6-fluoro-1H-indazole (98% yield). 1H NMR (400 MHz, CDCl3) d 1.33 (t, 3, J=7.7), 1.35-1.44 (m, 2), 1.47-1.96 (m, 8), 2.93 (q, 2, J=7.7), 4.14-4.22 (m, 1), 6.81 (dt, 1, J=8.9, 2.1), 6.99 (dd, 1, J=9.8, 2.1), 7.40 (ddd, 1, J=8.7, 5.2, 0.4). 13C NMR (100 MHz, CDCl3) d 13.97, 20.53, 25.37, 25.84, 32.32, 58.18, 94.77 (d, J=27.4), 109.11 (d, J=26.0), 119.38, 121.75 (d, J=11.5), 139.89 (d, J=13.0), 146.61, 161.95 (d, J=242).

후처리

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux in a Dean-Stark apparatus for 12 hours
  3. customThe toluene layer was separated
  4. washwashed with water (75 mL) and brine (75 mL)
  5. dry with materialThe organic layer was dried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated

출처 및 근거

ORD 기록
ord-db61696e0bf84900b117dc58b2730888
출처 데이터셋
uspto-grants-1999_12
특허 번호
US06005118

연결된 노트

불러오는 중…