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

HRID 450637Notes

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]=[CH:20][C:21]=1[F:22])[C:16](O)=O)#[N:12].N>>[F:22][C:21]1[CH:20]=[CH:19][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:14][C:13]=1[C:11]#[N:12]

Participants

Reactant 3

HCID 222Ammonia

HCID 308113N-Hydroxynicotinimidamide

HCID 27739323-Cyano-4-fluorobenzoic acid

Product 1

HCID 670260662-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-4-fluorobenzoic acid (Aldrich). 1H NMR (300 MHz, CD3OD) δ ppm 7.62-7.71 (m, 2 H), 8.54-8.63 (m, 2 H), 8.69 (dd, J=5.9, 2.2 Hz, 1 H), 8.75 (dd, J=4.9, 1.5 Hz, 1 H), 9.30 (dd, J=2.0, 1.0 Hz, 1 H); MS (DCI/NH3) m/z 267 (M+H)+.

Sources & evidence

ORD record: ord-04b88718c0c942dd8543f9ec4b85e120
Source dataset: uspto-grants-2013_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08486979B2

Reaction notes

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