3-(1-Bromo-ethyl)-5-(3-chloro-phenyl)-[1,2,4]oxadiazole → 4-(5-{2-[5-(3-chlorophenyl)-1,2,4-oxadiazol-3-yl]propyl}-4-cyclopropyl-4H-1,2,4-triazol-3-yl)pyridine

HRID 732134Notes

Reaction equation

[Li]CCCC.[CH:6]1([N:9]2[C:13]([CH3:14])=[N:12][N:11]=[C:10]2[C:15]2[CH:20]=[CH:19][N:18]=[CH:17][CH:16]=2)[CH2:8][CH2:7]1.Br[CH:22]([C:24]1[N:28]=[C:27]([C:29]2[CH:34]=[CH:33][CH:32]=[C:31]([Cl:35])[CH:30]=2)[O:26][N:25]=1)[CH3:23]>C1COCC1>[Cl:35][C:31]1[CH:30]=[C:29]([C:27]2[O:26][N:25]=[C:24]([CH:22]([CH3:23])[CH2:14][C:13]3[N:9]([CH:6]4[CH2:8][CH2:7]4)[C:10]([C:15]4[CH:20]=[CH:19][N:18]=[CH:17][CH:16]=4)=[N:11][N:12]=3)[N:28]=2)[CH:34]=[CH:33][CH:32]=1

Participants

Conditions

Temperature: -78 °C

Procedure

n-BuLi (210 ml, 2.5 M in hex., 0.52 mmol) was added dropwise to a solution of 4-(4-cyclopropyl-5-methyl-4H-1,2,4-triazol-3-yl)pyridine (80 mg, 0.4 mmol) in THF (10 ml) at −78° C. under an atm. of nitrogen. After stirring for 15 min 3-(1-Bromo-ethyl)-5-(3-chloro-phenyl)-[1,2,4]oxadiazole (115 mg, 0.4 mmol) in THF (2 ml) was added. The mixture was stirred for 2 h at −78° C. and then at r.t. for 1 h. The solvent was removed under reduced pressure and the desired product was obtained by prep. HPLC in 20 mg yield. 1H NMR: 0.7 (m, 2 H) 1.2 (ddd, 2 H) 1.6 (d, 3 H) 3.2 (dd, 1 H) 3.3 (ddd, 1 H) 3.6 (dd, 1 H) 3.9 (m, 1 H) 7.5 (t, 1 H) 7.6 (m, 1 H) 7.7 (m, 2 H) 8.0 (m, 1 H) 8.1 (t, 1 H) 8.7 (m, 2 H)

Workup

additionwas added
waitat r.t. for 1 h
customThe solvent was removed under reduced pressure

Sources & evidence

ORD record: ord-1682a81c682e4aef8633690c7b70eab5
Source dataset: uspto-grants-2009_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07585881B2

Reaction notes

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