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

HRID 390486Notes

Reaction equation

HRID 390486 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])=[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]=[N: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 86636847N-Hydroxypyrimidine-5-carbimidoyl chloride

Product 1

HCID 445464825-(3,4-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 4-ethynyl-1,2-difluorobenzene (Apollo, 69 mg, 0.5 mmol). 1H NMR (300 MHz, DMSO-d6) δ 7.71 (ddd, J=10.5, 8.3, 8.3 Hz, 1H), 7.77-7.86 (m, 2H), 8.04 (ddd, J=11.4, 7.6, 2.0 Hz, 1 H), 9.31 (s, 2H), 9.35 (s, 1H) ppm; MS (DCI/NH3) m/z 260 (M+H)+.

Sources & evidence

ORD record
ord-6f037090e1d441efb2bc86e676403ea8
Source dataset
uspto-grants-2013_02
Patent number
US08383658B2

Reaction notes

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