Ammonia → 3-Fluoro-5-(3-(pyridin-3-yl)-1,2,4-oxadiazol-5-yl)benzonitrile

HRID 578110Notes

Reaction equation

HRID 578110 reaction equation
[OH:1][N:2]=[C:3]([NH2:10])[C:4]1[CH:9]=[CH:8][CH:7]=[N:6][CH:5]=1.[C:11]([C:13]1[CH:14]=[C:15]([CH:19]=[C:20]([F:22])[CH:21]=1)[C:16](O)=O)#[N:12].N>>[F:22][C:20]1[CH:21]=[C:13]([CH:14]=[C:15]([C:16]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:19]=1)[C:11]#[N:12]

Participants

4

Reactant 3

HCID 222AmmoniaHCID 308113N-HydroxynicotinimidamideHCID 27579633-Cyano-5-fluorobenzoic acid

Product 1

HCID 670262123-Fluoro-5-(3-(pyridin-3-yl)-1,2,4-oxadiazol-5-yl)benzonitrile

Procedure

The title compound was prepared according to the procedure of Example 8 using N′-hydroxynicotinimidamide (Aldrich) and 3-cyano-5-fluorobenzoic acid (Aldrich). 1H NMR (300 MHz, CD3OD) δ 7.65 (ddd, J=8.0, 5.1, 0.8 Hz, 1H), 7.95 (ddd, J=8.1, 2.6, 1.6 Hz, 1H), 8.32 (ddd, J=8.7, 2.6, 1.4 Hz, 1H), 8.46 (t, J=1.4 Hz, 1H), 8.58 (ddd, J=8.1, 2.0, 1.8 Hz, 1H), 8.76 (dd, J=5.2, 1.6 Hz, 1H), 9.31 (dd, J=2.0, 0.8 Hz, 1H) ppm; MS (DCI/NH3) m/z 267 (M+H)+.

Sources & evidence

ORD record
ord-84828af9107a4aaaaf1408e8fa9c2fb6
Source dataset
uspto-grants-2015_05
Patent number
US09040568B2

Reaction notes

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