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 732078ノート

反応式

HRID 732078 の反応式
[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

参加物

5

反応物 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

生成物 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)-pyridine収率 10%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

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)

後処理

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

出典と根拠

ORDレコード
ord-0786664720a34450b9455f73beab4487
出典データセット
uspto-grants-2009_09
特許番号
US07585881B2

反応ノート

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