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

HRID 390448Notes

Reaction equation

HRID 390448 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])=[C:15]([F:20])[CH:14]=1)#[CH:12].N>>[F:20][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]=[CH:17][C:16]=1[F:19]

Participants

4

Reactant 3

HCID 222AmmoniaHCID 138784543,4-DifluorophenylacetyleneHCID 53404818N-Hydroxy-3-pyridinecarboximidoyl chloride

Product 1

HCID 445462295-(3,4-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 4-ethynyl-1,2-difluorobenzene (Apollo, 69 mg, 0.5 mmol). 1H NMR (300 MHz, DMSO-d6) δ 7.60-7.75 (m, 2H), 7.76-7.85 (m, 2H), 8.05 (ddd, J=11.4, 7.6, 2.4 Hz, 1H), 8.37 (dt, J=7.9, 2.0 Hz, 1H), 8.78 (dd, J=5.1, 1.7 Hz, 1H), 9.14 (d, J=1.7 Hz, 1H) ppm; MS (DCI/NH3) m/z 259 (M+H)+.

Sources & evidence

ORD record
ord-c5f351d8e6b64715a73dea50d5adfea0
Source dataset
uspto-grants-2013_02
Patent number
US08383658B2

Reaction notes

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