Ammonia → 5-(3-Chlorophenyl)-3-(6-chloropyridin-3-yl)isoxazole

HRID 390529Notes

Reaction equation

HRID 390529 reaction equation
[Cl:1][C:2]1[CH:11]=[CH:10][C:5]([C:6](Cl)=[N:7][OH:8])=[CH:4][N:3]=1.[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:8][N:7]=[C:6]([C:5]3[CH:4]=[N:3][C:2]([Cl:1])=[CH:11][CH:10]=3)[CH:20]=2)[CH:16]=[CH:17][CH:18]=1

Participants

4

Reactant 3

HCID 222AmmoniaHCID 1230861-Chloro-3-ethynylbenzeneHCID 765731256-Chloro-N-hydroxynicotinimidoyl chloride

Product 1

HCID 445456875-(3-Chlorophenyl)-3-(6-chloropyridin-3-yl)isoxazole

Procedure

The titled compound was prepared according to Method CB using the product of Example 95B (79 mg, 0.5 mmol) and 1-chloro-3-ethynylbenzene (Apollo, 68 mg, 0.5 mmol). 1H NMR (300 MHz, CDCl3) δ6.88 (s, 1H), 7.43-7.52 (m, 3H), 7.69-7.78 (m, 1H), 7.81-7.89 (m, 1H), 8.18 (dd, J=8.3, 2.4 Hz, 1H), 8.84 (d, J=2.8 Hz, 1H) ppm; MS (DCI/NH3) m/z 291 (M+H)+, 293 (M+H)+.

Sources & evidence

ORD record
ord-2f02d6f46b2b4464ab8079d8b68987cd
Source dataset
uspto-grants-2013_02
Patent number
US08383658B2

Reaction notes

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