Ammonia → 3-(5-Fluoropyridin-3-yl)-5-(pyridin-3-yl)isoxazole

HRID 390460

Reaction equation

HRID 390460 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].[C:12]([C:14]1[CH:15]=[N:16][CH:17]=[CH:18][CH:19]=1)#[CH:13].N>>[F:1][C:2]1[CH:11]=[C:6]([C:7]2[CH:13]=[C:12]([C:14]3[CH:15]=[N:16][CH:17]=[CH:18][CH:19]=3)[O:9][N:8]=2)[CH:5]=[N:4][CH:3]=1

Participants

4

Reactant 3

HCID 222AmmoniaHCID 1860033-EthynylpyridineHCID 866368465-Fluoro-N-hydroxynicotinimidoyl chloride

Product 1

HCID 690062403-(5-Fluoropyridin-3-yl)-5-(pyridin-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 3-ethynylpyridine (Aldrich, 52 mg, 0.5 mmol). 1H NMR (300 MHz, MeOH-d4) 87.59 (s, 1H), 7.63 (ddd, J=8.0, 5.1, 0.8 Hz, 1H), 8.19 (ddd, J=9.3, 2.8, 1.8 Hz, 1H), 8.36 (dt, J=7.9, 2.0 Hz, 1H), 8.62 (d, J=2.8 Hz, 1H), 8.68 (dd, J=5.2, 1.6 Hz, 1H), 8.99 (t, J=1.6 Hz, 1H), 9.12 (d, J=2.4 Hz, 1H) ppm; MS (DCI/NH3) m/z 242 (M+H)+.

Sources & evidence

ORD record
ord-1e314d494b214b1bb5913b2d90e608e3
Source dataset
uspto-grants-2013_02
Patent number
US08383658B2

Linked notes

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