Ammonia → 5-(3-Chlorophenyl)-3-(5-chloropyridin-3-yl)isoxazole

HRID 390511Notes

Reaction equation

HRID 390511 reaction equation
[Cl: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:18]=[CH:17][CH:16]=[C:15]([C:19]#[CH:20])[CH:14]=1.N>>[Cl:12][C:13]1[CH:14]=[C:15]([C:19]2[O:9][N:8]=[C:7]([C:6]3[CH:5]=[N:4][CH:3]=[C:2]([Cl:1])[CH:11]=3)[CH:20]=2)[CH:16]=[CH:17][CH:18]=1

Participants

4

Reactant 3

HCID 222AmmoniaHCID 1230861-Chloro-3-ethynylbenzeneHCID 866368495-Chloro-N-hydroxynicotinimidoyl chloride

Product 1

HCID 445455465-(3-Chlorophenyl)-3-(5-chloropyridin-3-yl)isoxazole

Procedure

The titled compound was prepared according to Method CB using the product of Example 69B (57 mg, 0.3 mmol) and 1-chloro-3-ethynylbenzene (Apollo, 41 mg, 0.3 mmol). 1H NMR (300 MHz, DMSO-d6) δ 7.61-7.68 (m, 2H), 7.85-7.89 (m, 1H), 7.90 (s, 1H), 7.96-8.00 (m, 1H), 8.43 (t, J=2.1 Hz, 1H), 8.81 (d, J=2.4 Hz, 1H), 9.08 (d, J=1.6 Hz, 1H) ppm; MS (DCI/NH3) m/z 291 (M+H)+, 293 (M+H)+.

Sources & evidence

ORD record
ord-fe879dbe8e3b464b8f8bf99b16b41613
Source dataset
uspto-grants-2013_02
Patent number
US08383658B2

Reaction notes

Loading…