Ammonia → 3-(5-Chloropyridin-3-yl)-5-(4-fluoro-3-methylphenyl)isoxazole

HRID 390514

Reaction equation

HRID 390514 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].[C:12]([C:14]1[CH:19]=[CH:18][C:17]([F:20])=[C:16]([CH3:21])[CH:15]=1)#[CH:13].N>>[Cl:1][C:2]1[CH:11]=[C:6]([C:7]2[CH:13]=[C:12]([C:14]3[CH:19]=[CH:18][C:17]([F:20])=[C:16]([CH3:21])[CH:15]=3)[O:9][N:8]=2)[CH:5]=[N:4][CH:3]=1

Participants

4

Reactant 3

HCID 222AmmoniaHCID 162137974-Ethynyl-1-fluoro-2-methylbenzeneHCID 866368495-Chloro-N-hydroxynicotinimidoyl chloride

Product 1

HCID 445456123-(5-Chloropyridin-3-yl)-5-(4-fluoro-3-methylphenyl)isoxazole

Procedure

The titled compound was prepared according to Method CB using the product of Example 69B (57 mg, 0.3 mmol) and 4-ethynyl-1-fluoro-2-methylbenzene (Aldrich, 40 mg, 0.3 mmol). 1H NMR (300 MHz, DMSO-d6) δ2.34 (d, J=2.0 Hz, 3H), 7.38 (t, J=9.2 Hz, 1H), 7.72 (s, 1H), 7.74-7.81 (m, 1H), 7.84-7.91 (m, 1H), 8.42 (t, J=2.1 Hz, 1H), 8.80 (d, J=2.4 Hz, 1H), 9.07 (d, J=1.7 Hz, 1H) ppm; MS (DCI/NH3) m/z 289 (M+H)+, 291 (M+H)+.

Sources & evidence

ORD record
ord-aabd6e9b5fae424daa6ed15c1771e622
Source dataset
uspto-grants-2013_02
Patent number
US08383658B2

Linked notes

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