Potassium Carbonate → 1-[1-(4-Fluorophenyl)-5-isopropylpyrazol-4-yl]-3-[5-methyl-3-(trifluoromethyl)pyrazol-1-yl]pyrrolidin-2-one

HRID 522319노트

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HRID 522319 반응식
Br[CH:2]1[CH2:6][CH2:5][N:4]([C:7]2[CH:8]=[N:9][N:10]([C:15]3[CH:20]=[CH:19][C:18]([F:21])=[CH:17][CH:16]=3)[C:11]=2[CH:12]([CH3:14])[CH3:13])[C:3]1=[O:22].[CH3:23][C:24]1[NH:28][N:27]=[C:26]([C:29]([F:32])([F:31])[F:30])[CH:25]=1.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[F:21][C:18]1[CH:19]=[CH:20][C:15]([N:10]2[C:11]([CH:12]([CH3:14])[CH3:13])=[C:7]([N:4]3[CH2:5][CH2:6][CH:2]([N:28]4[C:24]([CH3:23])=[CH:25][C:26]([C:29]([F:32])([F:31])[F:30])=[N:27]4)[C:3]3=[O:22])[CH:8]=[N:9]2)=[CH:16][CH:17]=1

참가 물질

5

반응물 3

HCID 11430Potassium CarbonateHCID 1390771H-Pyrazole, 3-methyl-5-(trifluoromethyl)-HCID 867230343-Bromo-1-[1-(4-fluorophenyl)-5-isopropylpyrazol-4-yl]pyrrolidin-2-one

생성물 1

HCID 867230331-[1-(4-Fluorophenyl)-5-isopropylpyrazol-4-yl]-3-[5-methyl-3-(trifluoromethyl)pyrazol-1-yl]pyrrolidin-2-one수율 80.2%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

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온도
60 °C

실험 절차

A mixture of 3-bromo-1-[1-(4-fluorophenyl)-5-isopropylpyrazol-4-yl]pyrrolidin-2-one (0.023 g, 0.063 mmol), 5-methyl-3-(trifluoromethyl)-1H-pyrazole (0.040 g, 0.27 mmol) and K2CO3 (0.060 g, 0.43 mmol) in DMF (1 mL) was stirred at 60° C. for 1 hr. It was then cooled to room temperature, quenched with water (30 mL) and extracted with EtOAc (100 mL). The organic layer was separated, dried over anhydrous sodium sulfate, concentrated in vacuo and purified by flash chromatography (SiO2, 0˜100% EtOAc/hexanes gradient elution) to give the title compound (0.022 g, 80%). 1H NMR (400 MHz, CDCl3) δ 7.52 (s, 1H), 7.37 (dd, J=9.2, 4.8 Hz, 2H), 7.17 (dd, J=8.6, 8.6 Hz, 2H), 6.32 (s, 1H), 5.05 (dd, J=9.2, 5.6 Hz, 1H), 4.07 (m, 1H), 3.80 (m, 1H), 2.84-3.02 (m, 2H), 2.74 (m, 1H), 2.45 (s, 3H), 1.21 (d, J=7.6 Hz, 3H), 1.11 (d, J=6.8 Hz, 3H); MS: (ES) m/z calculated for C21H21F4N5O [M+H]+ 436.1. found 436.1.

후처리

  1. temperatureIt was then cooled to room temperature
  2. customquenched with water (30 mL)
  3. extractionextracted with EtOAc (100 mL)
  4. customThe organic layer was separated
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated in vacuo
  7. custompurified by flash chromatography (SiO2, 0˜100% EtOAc/hexanes gradient elution)

출처 및 근거

ORD 기록
ord-0b9528e3c70447f8af9c9ace65251521
출처 데이터셋
uspto-grants-2016_05
특허 번호
US09328116B2

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