Ammonia → 3-Chloro-5-(3-(5-fluoropyridin-3-yl)isoxazol-5-yl)benzonitrile

HRID 390498Notes

Reaction equation

HRID 390498 reaction equation
[F:1][C:2]1[CH:3]=[N:4][CH:5]=[C:6]([CH:11]=1)[C:7](Cl)=[N:8][OH:9].[Cl:12][C:13]1[CH:14]=[C:15]([CH:18]=[C:19]([C:21]#[CH:22])[CH:20]=1)[C:16]#[N:17].N>>[Cl:12][C:13]1[CH:14]=[C:15]([CH:18]=[C:19]([C:21]2[O:9][N:8]=[C:7]([C:6]3[CH:5]=[N:4][CH:3]=[C:2]([F:1])[CH:11]=3)[CH:22]=2)[CH:20]=1)[C:16]#[N:17]

Participants

4

Reactant 3

HCID 222AmmoniaHCID 866368465-Fluoro-N-hydroxynicotinimidoyl chlorideHCID 866368483-Chloro-5-ethynylbenzonitrile

Product 1

HCID 445456883-Chloro-5-(3-(5-fluoropyridin-3-yl)isoxazol-5-yl)benzonitrile

Procedure

The titled compound was prepared according to Method CB using the product of Example 28B (88 mg, 0.5 mmol) and the product of Example 66A (82 mg, 0.5 mmol). 1H NMR (300 MHz, MeOH-d4) δ 8.00 (s, 1H), 8.22 (ddd, J=9.5, 2.7, 1.7 Hz, 1H), 8.26 (dd, J=2.0, 1.4 Hz, 1H), 8.33 (t, J=1.7 Hz, 1H), 8.40 (t, J=1.5 Hz, 1H), 8.79 (d, J=2.7 Hz, 1H), 8.98 (t, J=1.7 Hz, 1H) ppm; MS (DCI/NH3) m/z 300 (M+H)+, 302 (M+H)+.

Sources & evidence

ORD record
ord-476f0d6110a640f68a2bb05c453b9b38
Source dataset
uspto-grants-2013_02
Patent number
US08383658B2

Reaction notes

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