Potassium Carbonate → phenyl 1-(4-fluorophenyl)-3-(trifluoromethyl)-1H-pyrazol-5-ylcarbamate

HRID 631499노트

반응식

HRID 631499 반응식
[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:12]([NH2:13])=[CH:11][C:10]([C:14]([F:17])([F:16])[F:15])=[N:9]2)=[CH:4][CH:3]=1.C([O-])([O-])=O.[K+].[K+].Cl[C:25]([O:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)=[O:26]>C1COCC1>[F:1][C:2]1[CH:3]=[CH:4][C:5]([N:8]2[C:12]([NH:13][C:25](=[O:26])[O:27][C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)=[CH:11][C:10]([C:14]([F:15])([F:17])[F:16])=[N:9]2)=[CH:6][CH:7]=1

참가 물질

5

반응물 3

HCID 11430Potassium CarbonateHCID 15891Phenyl chloroformateHCID 508964961-(4-fluorophenyl)-3-(trifluoromethyl)-1H-pyrazol-5-amine

생성물 1

HCID 67159315phenyl 1-(4-fluorophenyl)-3-(trifluoromethyl)-1H-pyrazol-5-ylcarbamate수율 79.3%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

According to the procedure described in Example 161C, to a solution of 1-(4-fluorophenyl)-3-(trifluoromethyl)-1H-pyrazol-5-amine (2.346 g, 9.57 mmol) in THF (25 mL) and K2CO3 (2.63 g, 19 mmol) was added phenyl chloroformate (1.948 g, 12.4 mmol). The crude product was purified by silica gel chromatography (with 5-20% EtOAc/hexane as eluants) to afford phenyl 1-(4-fluorophenyl)-3-(trifluoromethyl)-1H-pyrazol-5-ylcarbamate as solid (2.772 g, 79%). 1H NMR (300 MHz, CDCl3) δ 7.54 (m, 2H), 7.40 (m, 2H), 7.27 (m, 3H), 7.14 (m, 2H), 6.97 (br, 1H), 6.85 (s, 1H); LC-MS (ESI) m/z 366 (M+H)+.

후처리

  1. customThe crude product was purified by silica gel chromatography (with 5-20% EtOAc/hexane as eluants)

출처 및 근거

ORD 기록
ord-b9aa3807ff414a82a8754609491898be
출처 데이터셋
uspto-grants-2016_04
특허 번호
US09320739B2

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