Ammonia → 5-(2-Chlorophenyl)-3-(5-fluoropyridin-3-yl)isoxazole

HRID 390475Notes

Reaction equation

HRID 390475 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:18]=[CH:17][CH:16]=[CH:15][C:14]=1[C:19]#[CH:20].N>>[Cl:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[C:19]1[O:9][N:8]=[C:7]([C:6]2[CH:5]=[N:4][CH:3]=[C:2]([F:1])[CH:11]=2)[CH:20]=1

Participants

4

Reactant 3

HCID 222AmmoniaHCID 5859951-Chloro-2-ethynylbenzeneHCID 866368465-Fluoro-N-hydroxynicotinimidoyl chloride

Product 1

HCID 445464165-(2-Chlorophenyl)-3-(5-fluoropyridin-3-yl)isoxazole

Procedure

The titled compound was prepared according to Method CB using the product of Example 28B (88 mg, 0.5 mmol) and 1-chloro-2-ethynylbenzene (Apollo, 68 mg, 0.5 mmol). 1H NMR (300 MHz, MeOH-d4) δ 7.48-7.54 (m, 2H), 7.56 (s, 1H), 7.59-7.68 (m, 1H), 7.97 (dd, J=5.9, 3.9 Hz, 1H), 8.21 (ddd, J=9.2, 2.7, 1.7 Hz, 1H), 8.61 (d, J=2.7 Hz, 1H), 9.00 (t, J=1.5 Hz, 1H) ppm; MS (DCI/NH3) m/z 277 (M+H)+, 275 (M+H)+.

Sources & evidence

ORD record
ord-6d08dc476c86468c87e75ac2aec472f7
Source dataset
uspto-grants-2013_02
Patent number
US08383658B2

Reaction notes

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