Ammonia → 5-(5-Bromopyridin-3-yl)-3-(pyridin-3-yl)-1,2,4-oxadiazole

HRID 713758Notes

Reaction equation

HRID 713758 reaction equation
[OH:1][N:2]=[C:3]([NH2:10])[C:4]1[CH:9]=[CH:8][CH:7]=[N:6][CH:5]=1.[Br:11][C:12]1[CH:13]=[N:14][CH:15]=[C:16]([CH:20]=1)[C:17](Cl)=O.N>>[Br:11][C:12]1[CH:20]=[C:16]([C:17]2[O:1][N:2]=[C:3]([C:4]3[CH:5]=[N:6][CH:7]=[CH:8][CH:9]=3)[N:10]=2)[CH:15]=[N:14][CH:13]=1

Participants

4

Reactant 3

HCID 222AmmoniaHCID 308113N-HydroxynicotinimidamideHCID 27812235-Bromonicotinoyl chloride

Product 1

HCID 597587515-(5-Bromopyridin-3-yl)-3-(pyridin-3-yl)-1,2,4-oxadiazole

Procedure

The title compound was prepared according to the procedure of Example 1 using N′-hydroxynicotinimidamide (Aldrich) and 5-bromonicotinoyl chloride (Alfa). 1H NMR (300 MHz, DMSO-d6) δ 8.65-8.69 (m, 1H), 8.45-8.49 (m, 1H), 8.79 (t, J=1.7 Hz, 1H), 8.84 (dd, J=1.7, 2.0 Hz, 1H), 9.07 (d, J=2 Hz, 1H), 9.28-9.29 (m, 1H), 9.34 (d, J=1.7 Hz, 1H) ppm; MS (DCl/NH3) m/z 303 (M+H)+.

Sources & evidence

ORD record
ord-598b79b546a5426a8892bf05cdca71e9
Source dataset
uspto-grants-2015_11
Patent number
US09186407B2

Reaction notes

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