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

HRID 390444Notes

Reaction equation

HRID 390444 reaction equation
[OH:1][N:2]=[C:3](Cl)[C:4]1[CH:9]=[CH:8][CH:7]=[N:6][CH:5]=1.[C:11]([C:13]1[CH:18]=[C:17]([O:19][CH3:20])[CH:16]=[C:15]([O:21][CH3:22])[CH:14]=1)#[CH:12].N>>[CH3:22][O:21][C:15]1[CH:14]=[C:13]([C:11]2[O:1][N:2]=[C:3]([C:4]3[CH:5]=[N:6][CH:7]=[CH:8][CH:9]=3)[CH:12]=2)[CH:18]=[C:17]([O:19][CH3:20])[CH:16]=1

Participants

4

Reactant 3

HCID 222AmmoniaHCID 46613211-Ethynyl-3,5-dimethoxybenzeneHCID 53404818N-Hydroxy-3-pyridinecarboximidoyl chloride

Product 1

HCID 445462255-(3,5-Dimethoxyphenyl)-3-(pyridin-3-yl)isoxazole

Procedure

The titled compound was prepared as the hydrochloride salt according to Method CB using the product of Example 1A (78 mg, 0.5 mmol) and 1-ethynyl-3,5-dimethoxybenzene (Aldrich, 81 mg, 0.5 mmol). 1H NMR (300 MHz, DMSO-d6) δ3.85 (s, 6H), 6.69 (t, J=2.2 Hz, 1H), 7.07 (d, J=2.4 Hz, 2H), 7.68 (ddd, J=8.0, 4.9, 1.0 Hz, 1H), 7.78 (s, 1H), 8.38 (dt, J=7.6, 1.9 Hz, 1H), 8.77 (dd, J=4.9, 1.5 Hz, 1H), 9.14 (d, J=1.4 Hz, 1H) ppm; MS (DCI/NH3) m/z 283 (M+H)+.

Sources & evidence

ORD record
ord-e1a24deffffd4bccb29ca99d071edb23
Source dataset
uspto-grants-2013_02
Patent number
US08383658B2

Reaction notes

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