Ammonia → 5-(2,4-Difluorophenyl)-3-(pyridin-3-yl)isoxazole

HRID 390446Notes

Reaction equation

HRID 390446 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]=[CH:17][C:16]([F:19])=[CH:15][C:14]=1[F:20])#[CH:12].N>>[F:20][C:14]1[CH:15]=[C:16]([F:19])[CH:17]=[CH:18][C:13]=1[C:11]1[O:1][N:2]=[C:3]([C:4]2[CH:5]=[N:6][CH:7]=[CH:8][CH:9]=2)[CH:12]=1

Participants

4

Reactant 3

HCID 222AmmoniaHCID 50638201-Ethynyl-2,4-difluorobenzeneHCID 53404818N-Hydroxy-3-pyridinecarboximidoyl chloride

Product 1

HCID 445462275-(2,4-Difluorophenyl)-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-2,4-difluorobenzene (Aldrich, 69 mg, 0.5 mmol). 1H NMR (300 MHz, DMSO-d6) δ 7.29-7.43 (m, 1H), 7.53-7.65 (m, 2H), 7.69 (dd, J=7.5, 4.7 Hz, 1H), 8.08 (td, J=8.7, 6.3 Hz, 1H), 8.48 (dt, J=7.9, 2.0 Hz, 1H), 8.78 (dd, J=4.9, 1.5 Hz, 1H), 9.23 (d, J=1.7 Hz, 1H) ppm; MS (DCI/NH3) m/z 259 (M+H)+.

Sources & evidence

ORD record
ord-06b91505ed964a7eb6601e5bb2bb727e
Source dataset
uspto-grants-2013_02
Patent number
US08383658B2

Reaction notes

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