Ammonia → 5-(3,5-Dimethoxyphenyl)-3-(5-fluoropyridin-3-yl)isoxazole

HRID 390497Notes

Reaction equation

HRID 390497 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:19]=[C:18]([O:20][CH3:21])[CH:17]=[C:16]([O:22][CH3:23])[CH:15]=1)#[CH:13].N>>[CH3:23][O:22][C:16]1[CH:15]=[C:14]([C:12]2[O:9][N:8]=[C:7]([C:6]3[CH:5]=[N:4][CH:3]=[C:2]([F:1])[CH:11]=3)[CH:13]=2)[CH:19]=[C:18]([O:20][CH3:21])[CH:17]=1

Participants

4

Reactant 3

HCID 222AmmoniaHCID 46613211-Ethynyl-3,5-dimethoxybenzeneHCID 866368465-Fluoro-N-hydroxynicotinimidoyl chloride

Product 1

HCID 445465445-(3,5-Dimethoxyphenyl)-3-(5-fluoropyridin-3-yl)isoxazole

Procedure

The titled compound was prepared according to Method CB using the product of product of Example 28B (88 mg, 0.5 mmol) and 1-ethynyl-3,5-dimethoxybenzene (Aldrich, 81 mg, 0.5 mmol). 1H NMR (300 MHz, MeOH-d4) 83.87 (s, 6H), 6.64 (t, J=2.2 Hz, 1H), 7.06 (d, J=2.4 Hz, 2H), 7.40 (s, 1H), 8.16 (ddd, J=9.2, 2.7, 1.7 Hz, 1H), 8.60 (d, J=2.7 Hz, 1H), 8.96 (t, J=1.5 Hz, 1H) ppm; MS (DCI/NH3) m/z 301 (M+H)+.

Sources & evidence

ORD record
ord-27a9755067294451ac08a834d733d829
Source dataset
uspto-grants-2013_02
Patent number
US08383658B2

Reaction notes

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