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

HRID 390433

Reaction equation

HRID 390433 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:14]=[N:15][CH:16]=[CH:17][CH:18]=1)#[CH:12].N>>[N:6]1[CH:7]=[CH:8][CH:9]=[C:4]([C:3]2[CH:12]=[C:11]([C:13]3[CH:14]=[N:15][CH:16]=[CH:17][CH:18]=3)[O:1][N:2]=2)[CH:5]=1

Participants

4

Reactant 3

HCID 222AmmoniaHCID 1860033-EthynylpyridineHCID 53404818N-Hydroxy-3-pyridinecarboximidoyl chloride

Product 1

HCID 145933323,5-Di(pyridin-3-yl)isoxazole

Procedure

The titled compound was prepared as the bishydrochloride salt according to Method CA using the product of Example 1A (0.78 g, 5.0 mmol) and 3-ethynylpyridine (Aldrich, 0.52 g, 5.0 mmol). 1H NMR (300 MHz, DMSO-d6) δ 7.76 (dd, J=8.1, 5.1 Hz, 1H), 7.79-7.86 (m, 1H), 7.98 (s, 1H), 8.44 (dt, J=8.0, 2.0, 1.9 Hz, 1H), 8.55 (dt, J=8.1, 1.9 Hz, 1H), 8.80 (dd, J=4.9, 1.5 Hz, 1H), 8.86 (dd, J=5.1, 1.7 Hz, 1H), 9.21 (d, J=2.0 Hz, 1H), 9.23 (d, J=2.0 Hz, 1H) ppm; MS (DCI/NH3) m/z 224 (M+H)+.

Sources & evidence

ORD record
ord-7f076c8828724b3492713981d2642f36
Source dataset
uspto-grants-2013_02
Patent number
US08383658B2

Linked notes

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