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

HRID 390478Notes

Reaction equation

HRID 390478 reaction equation
[OH:1][N:2]=[C:3](Cl)[C:4]1[CH:5]=[N:6][CH:7]=[N:8][CH:9]=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]=[N:8][CH:9]=2)[CH:12]=1

Participants

4

Reactant 3

HCID 222AmmoniaHCID 50638201-Ethynyl-2,4-difluorobenzeneHCID 86636847N-Hydroxypyrimidine-5-carbimidoyl chloride

Product 1

HCID 445464175-(2,4-Difluorophenyl)-3-(pyrimidin-5-yl)isoxazole

Procedure

The titled compound was prepared as the hydrochloride salt according to Method CB using the product of Example 44B (79 mg, 0.5 mmol) and 1-ethynyl-2,4-difluorobenzene (Aldrich, 69 mg, 0.5 mmol). 1H NMR (300 MHz, DMSO-d6) δ 7.30-7.42 (m, 1H), 7.61 (ddd, J=11.5, 9.1, 2.4 Hz, 1H), 7.68 (d, J=3.2 Hz, 1H), 8.08 (td, J=8.6, 6.5 Hz, 1H), 9.35 (s, 1H), 9.39 (s, 2H) ppm; MS (DCI/NH3) m/z 260 (M+H)+.

Sources & evidence

ORD record
ord-cccfc56def214896b2f2adf4e6d68a3f
Source dataset
uspto-grants-2013_02
Patent number
US08383658B2

Reaction notes

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