Pyridine, 4-(4,5-dimethyl-4H-1,2,4-triazol-3-yl)- → 4-(5-{2-[5-(3-Chloro-phenyl)-[1,2,4]oxadiazol-3-yl]-propyl}-4-methyl-4H-[1,2,4]triazol-3-yl)-pyridine

HRID 273166노트

반응식

HRID 273166 반응식
[Li]CCCC.[CH3:6][N:7]1[C:11]([CH3:12])=[N:10][N:9]=[C:8]1[C:13]1[CH:18]=[CH:17][N:16]=[CH:15][CH:14]=1.Br[CH:20]([C:22]1[N:26]=[C:25]([C:27]2[CH:32]=[CH:31][CH:30]=[C:29]([Cl:33])[CH:28]=2)[O:24][N:23]=1)[CH3:21]>C1COCC1>[Cl:33][C:29]1[CH:28]=[C:27]([C:25]2[O:24][N:23]=[C:22]([CH:20]([CH3:21])[CH2:12][C:11]3[N:7]([CH3:6])[C:8]([C:13]4[CH:18]=[CH:17][N:16]=[CH:15][CH:14]=4)=[N:9][N:10]=3)[N:26]=2)[CH:32]=[CH:31][CH:30]=1

참가 물질

5

반응물 3

HCID 11600754Pyridine, 4-(4,5-dimethyl-4H-1,2,4-triazol-3-yl)-HCID 578379313-(1-Bromo-ethyl)-5-(3-chloro-phenyl)-[1,2,4]oxadiazoleHCID 178418339Butyllithium

생성물 1

HCID 596673664-(5-{2-[5-(3-Chloro-phenyl)-[1,2,4]oxadiazol-3-yl]-propyl}-4-methyl-4H-[1,2,4]triazol-3-yl)-pyridine수율 10%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

84 microl (0.21 mmol, 2.5 M) n-BuLi was added dropwise to a solution of 37 mg (0.21 mmol) 4-(4,5-dimethyl-4H-[1,2,4]triazol-3-yl)-pyridine in 2.1 ml THF at 0° C. After 20 min a solution of 60 mg (0.21 mmol) 3-(1-bromo-ethyl)-5-(3-chloro-phenyl)-[1,2,4]oxadiazole was added dropwise. The reaction mixture was allowed to reach room temperature and stirred over night. NH4Cl(sat) was added and the mixture was extracted twice with EtOAc. The organic phase was dried and concentrated. Flashchromatography (CH2Cl2/MeOH 20:1) afforded 7.7 mg (10%) of the desired product. 1H NMR (CDCl3), d (ppm): 1.57 (d, 3 H) 3.16 (m, 1 H) 3.38 (m, 1 H) 3.71 (s, 3 H) 3.84 (d, 1 H) 7.46 (t, 1 H) 7.55 (m, 1 H) 7.58 (m, 2 H) 7.98 (m, 1 H) 8.10 (t, 1 H) 8.77 (d, 2 H)

후처리

  1. customto reach room temperature
  2. extractionthe mixture was extracted twice with EtOAc
  3. customThe organic phase was dried
  4. concentrationconcentrated

출처 및 근거

ORD 기록
ord-13dda66d8e6f454187b700922620fc93
출처 데이터셋
uspto-grants-2008_11
특허 번호
US07456200B2

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