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Water → ethyl 1-(2-fluorobenzyl)-5-(thiazol-2-yl)-1H-1,2,4-triazole-3-carboxylate

HRID 2174288
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반응식

HRID 2174288 반응식
[S:1]1[CH:5]=[CH:4][N:3]=[C:2]1[C:6]1[N:10]=[C:9]([C:11]([O:13][CH2:14][CH3:15])=[O:12])[NH:8][N:7]=1.[H-].[Na+].Br[CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=1[F:26].O>CN(C=O)C>[F:26][C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][C:20]=1[CH2:19][N:7]1[C:6]([C:2]2[S:1][CH:5]=[CH:4][N:3]=2)=[N:10][C:9]([C:11]([O:13][CH2:14][CH3:15])=[O:12])=[N:8]1.[F:26][C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][C:20]=1[CH2:19][N:8]1[C:9]([C:11]([O:13][CH2:14][CH3:15])=[O:12])=[N:10][C:6]([C:2]2[S:1][CH:5]=[CH:4][N:3]=2)=[N:7]1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

7

반응물 4

HCID 962WaterHCID 24758Sodium hydrideHCID 67968alpha-Bromo-o-fluorotolueneHCID 178470224HCID 178470224, 화합물

생성물 2

HCID 69093312ethyl 1-(2-fluorobenzyl)-5-(thiazol-2-yl)-1H-1,2,4-triazole-3-carboxylate수율 48%HCID 69094030ethyl 1-(2-fluorobenzyl)-3-(thiazol-2-yl)-1H-1,2,4-triazole-5-carboxylate
수율 44%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

To a solution of ethyl 3-(thiazol-2-yl)-1H-1,2,4-triazole-5-carboxylate (Intermediate-2, 1.7 mmol) in DMF (8 mL) was added sodium hydride (1.2 equiv). After 10 min, 1-(bromomethyl)-2-fluorobenzene (1.2 equiv) was added. The reaction was stirred at ambient temperature for 35 min. The reaction mixture was poured into water and extracted with EtOAc. The organic phases were washed with water and brine, dried over Na2SO4, filtered and conc. The crude product was purified using SiO2 chromatography and an appropriate solvent gradient (EtOAc/hexanes) to give ethyl 1-(2-fluorobenzyl)-5-(thiazol-2-yl)-1H-1,2,4-triazole-3-carboxylate (48%) and ethyl 1-(2-fluorobenzyl)-3-(thiazol-2-yl)-1H-1,2,4-triazole-5-carboxylate as white solids (44% yield).

후처리

  1. extractionextracted with EtOAc
  2. washThe organic phases were washed with water and brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. customconc. The crude product was purified

출처 및 근거

ORD 기록
ord-42b9f11f066d4ce098729872d3a3bad8
출처 데이터셋
uspto-grants-2015_06
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09061030B2

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