Ammonia → 5-(4-Bromophenyl)-3-(5-fluoropyridin-3-yl)isoxazole

HRID 390465

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

Participants

Reactant 3

HCID 222Ammonia

HCID 136603Benzene, 1-bromo-4-ethynyl-

HCID 866368465-Fluoro-N-hydroxynicotinimidoyl chloride

Product 1

HCID 445463475-(4-Bromophenyl)-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-bromo-4-ethynylbenzene (Alfa Aesar, 80 mg, 0.5 mmol). 1H NMR (300 MHz, MeOH-d4) δ 7.43 (s, 1H), 7.72 (dt, J=8.9, 2.2 Hz, 2H), 7.85 (dt, J=8.9, 2.2 Hz, 2H), 8.17 (ddd, J=9.5, 2.7, 1.7 Hz, 1H), 8.61 (d, J=2.7 Hz, 1H), 8.96 (t, J=1.5 Hz, 1H) ppm; MS (DCI/NH3) m/z 320 (M+H)+, 318 (M+H)+.

Sources & evidence

ORD record: ord-b46e8c42c57d42568a42360aef1df74d
Source dataset: uspto-grants-2013_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08383658B2

Linked notes

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