Ammonia → 3-(6-Chloropyridin-3-yl)-5-(2,4-difluorophenyl)isoxazole

HRID 390528Notes

Reaction equation

HRID 390528 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.[C:12]([C:14]1[CH:19]=[CH:18][C:17]([F:20])=[CH:16][C:15]=1[F:21])#[CH:13].N>>[Cl:1][C:2]1[N:3]=[CH:4][C:5]([C:6]2[CH:13]=[C:12]([C:14]3[CH:19]=[CH:18][C:17]([F:20])=[CH:16][C:15]=3[F:21])[O:8][N:7]=2)=[CH:10][CH:11]=1

Participants

4

Reactant 3

HCID 222AmmoniaHCID 50638201-Ethynyl-2,4-difluorobenzeneHCID 765731256-Chloro-N-hydroxynicotinimidoyl chloride

Product 1

HCID 445456863-(6-Chloropyridin-3-yl)-5-(2,4-difluorophenyl)isoxazole

Procedure

The titled compound was prepared according to Method CB using the product of Example 95B (79 mg, 0.5 mmol) and 1-ethynyl-2,4-difluorobenzene (Aldrich, 68 mg, 0.5 mmol). 1H NMR (300 MHz, CDCl3) δ 6.93-7.14 (m, 3H), 7.47 (d, J=7.5 Hz, 1H), 8.02 (td, J=8.6, 6.3 Hz, 1H), 8.18 (dd, J=8.1, 2.7 Hz, 1H), 8.86 (dd, J=2.5, 0.8 Hz, 1H) ppm; MS (DCI/NH3) m/z 293 (M+H)+, 295 (M+H)+.

Sources & evidence

ORD record
ord-6cb2867052af4f6096c6de81cb47e6fd
Source dataset
uspto-grants-2013_02
Patent number
US08383658B2

Reaction notes

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