Ammonia → 5-Phenyl-3-(pyrazin-2-yl)isoxazole

HRID 390522Notes

Reaction equation

HRID 390522 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][CH:16]=[CH:15][CH:14]=1)#[CH:12].N>>[C:13]1([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][CH:16]=[CH:15][CH:14]=1

Participants

4

Reactant 3

HCID 222AmmoniaHCID 10821PhenylacetyleneHCID 136395910N-Hydroxypyrazine-2-carbimidoyl chloride

Product 1

HCID 445456185-Phenyl-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 1-ethynyl-benzene (Aldrich, 52 mg, 0.5 mmol). 1H NMR (300 MHz, MeOH-d4) δ 7.41 (s, 1H), 7.47-7.70 (m, 3H), 7.86-8.08 (m, 2H), 8.70 (d, J=2.4 Hz, 1H), 8.76 (dd, J=2.8, 1.6 Hz, 1H), 9.29 (d, J=1.2 Hz, 1H) ppm; MS (DCI/NH3) m/z 224 (M+H)+.

Sources & evidence

ORD record
ord-58bfa44ff3034a1faf899e8143ee58a0
Source dataset
uspto-grants-2013_02
Patent number
US08383658B2

Reaction notes

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