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

HRID 390525Notes

Reaction equation

HRID 390525 reaction equation
[OH:1][N:2]=[C:3](Cl)[C:4]1[CH:9]=[N:8][CH:7]=[CH:6][N: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:9]=[N:8][CH:7]=[CH:6][N:5]=3)[CH:12]=2)[CH:18]=[CH:17][C:16]=1[F:19]

Participants

4

Reactant 3

HCID 222AmmoniaHCID 138784543,4-DifluorophenylacetyleneHCID 136395910N-Hydroxypyrazine-2-carbimidoyl chloride

Product 1

HCID 445456835-(3,4-Difluorophenyl)-3-(pyrazin-2-yl)isoxazole

Procedure

The titled compound was prepared according to Method CB using the product of Example 83D (79 mg, 0.5 mmol) and 4-ethynyl-1,2-difluorobenzene (Apollo, 69 mg, 0.5 mmol). 1H NMR (300 MHz, MeOH-d4) δ 7.38-7.54 (m, 2H), 7.74-7.84 (m, 1H), 7.90 (ddd, J=11.1, 7.5, 2.0 Hz, 1H), 8.70 (d, J=2.4 Hz, 1H), 8.76 (dd, J=2.4, 1.6 Hz, 1H), 9.29 (d, J=1.6 Hz, 1H) ppm; MS (DCI/NH3) m/z 260 (M+H)+.

Sources & evidence

ORD record
ord-9b36bfde5093462481d5a679766c2cdd
Source dataset
uspto-grants-2013_02
Patent number
US08383658B2

Reaction notes

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