Ammonia → 5-(3,4,5-Trifluorophenyl)-3-(pyridin-3-yl)isoxazole

HRID 390449Notes

Reaction equation

HRID 390449 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]=[C:15]([F:21])[C:16]([F:20])=[C:17]([F:19])[CH:18]=1)#[CH:12].N>>[F:19][C:17]1[CH:18]=[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:14]=[C:15]([F:21])[C:16]=1[F:20]

Participants

4

Reactant 3

HCID 222AmmoniaHCID 227090715-Ethynyl-1,2,3-trifluorobenzeneHCID 53404818N-Hydroxy-3-pyridinecarboximidoyl chloride

Product 1

HCID 445114635-(3,4,5-Trifluorophenyl)-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 5-ethynyl-1,2,3-trifluorobenzene (Apollo, 78 mg, 0.5 mmol). 1H NMR (300 MHz, DMSO-d6) δ 7.69 (dd, J=7.9, 4.8 Hz, 1H), 7.85 (s, 1H), 7.95 (dd, J=8.7, 6.7 Hz, 2H), 8.35 (dt, J=8.1, 1.7 Hz, 1H), 8.79 (d, J=3.6 Hz, 1H), 9.11 (s, 1H) ppm; MS (DCI/NH3) m/z 277 (M+H)+.

Sources & evidence

ORD record
ord-ea0815c2e5784125ad4db2bc868a599e
Source dataset
uspto-grants-2013_02
Patent number
US08383658B2

Reaction notes

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