Water → 1-[2-(Trifluorometyl)phenyl]-3-(1-methyl-4-piperidinyl)-1H-indazole

HRID 867695

반응식

HRID 867695 반응식
[H-].[Na+].[CH3:3][N:4]1[CH2:9][CH2:8][CH:7]([C:10]2[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[NH:12][N:11]=2)[CH2:6][CH2:5]1.F[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=1[C:26]([F:29])([F:28])[F:27].O>CN(C)C=O>[F:27][C:26]([F:29])([F:28])[C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][C:20]=1[N:12]1[C:13]2[C:18](=[CH:17][CH:16]=[CH:15][CH:14]=2)[C:10]([CH:7]2[CH2:6][CH2:5][N:4]([CH3:3])[CH2:9][CH2:8]2)=[N:11]1

참가 물질

6

반응물 4

HCID 962WaterHCID 9807Benzene, 1-fluoro-2-(trifluoromethyl)-HCID 24758Sodium hydrideHCID 178480237HCID 178480237, 화합물

생성물 1

HCID 140325421-[2-(Trifluorometyl)phenyl]-3-(1-methyl-4-piperidinyl)-1H-indazole수율 24%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매2회

실험 절차

To a stirred suspension 1.0 g of a 50% oil dispersion of sodium hydride in 20 ml of dimethylformamide was added, dropwise, 3.2 g of 3-(1-methyl-4-piperidinyl)-1H-indazole dissolved in 25 ml of hot dimethylformamide. After stirring for one hr at ambient temperature, 3.75 ml of 2-fluorobenzotrifluoride was added. The reaction mixture was heated to 90° C. and stirred for 17 hrs. The mixture was then poured into water, extracted with ether, dried over anhydrous magnesium sulfate and concentrated. The residue was purified using flash chromatography (silica gel, diethylamine-ethyl acetate, 1:9). The appropriate fractions were evaporated. The residue was recrystallized once from hexane, then combined with a previously prepared sample (1.1 g), and recrystallized from hexane to yield 2.17 g (24%) of product, mp 110°-111° C.

후처리

  1. temperatureThe reaction mixture was heated to 90° C.
  2. stirringstirred for 17 hrs
  3. extractionextracted with ether
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated
  6. customThe residue was purified
  7. customThe appropriate fractions were evaporated
  8. customThe residue was recrystallized once from hexane
  9. customrecrystallized from hexane

출처 및 근거

ORD 기록
ord-e8705f9da10d40db9649ea31e7b58199
출처 데이터셋
uspto-grants-1988_10
특허 번호
US04775761

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