Ammonia → 3-Chloro-5-(3-(pyridin-3-yl)isoxazol-5-yl)benzonitrile

HRID 390499Notes

Reaction equation

HRID 390499 reaction equation
[OH:1][N:2]=[C:3](Cl)[C:4]1[CH:9]=[CH:8][CH:7]=[N:6][CH:5]=1.[Cl:11][C:12]1[CH:13]=[C:14]([CH:17]=[C:18]([C:20]#[CH:21])[CH:19]=1)[C:15]#[N:16].N>>[Cl:11][C:12]1[CH:13]=[C:14]([CH:17]=[C:18]([C:20]2[O:1][N:2]=[C:3]([C:4]3[CH:5]=[N:6][CH:7]=[CH:8][CH:9]=3)[CH:21]=2)[CH:19]=1)[C:15]#[N:16]

Participants

4

Reactant 3

HCID 222AmmoniaHCID 53404818N-Hydroxy-3-pyridinecarboximidoyl chlorideHCID 866368483-Chloro-5-ethynylbenzonitrile

Product 1

HCID 445465463-Chloro-5-(3-(pyridin-3-yl)isoxazol-5-yl)benzonitrile

Procedure

The titled compound was prepared according to Method CB using the product of Example 1A (78 mg, 0.5 mmol) and the product of Example 66A (82 mg, 0.5 mmol). 1H NMR (300 MHz, MeOH-d4) δ 7.62 (ddd, J=8.0, 4.9, 0.7 Hz, 1H), 7.97 (s, 1H), 8.24 (dd, J=2.0, 1.4 Hz, 1H), 8.28 (dt, J=8.1, 1.9 Hz, 1H), 8.34 (t, J=1.7 Hz, 1H), 8.41 (t, J=1.4 Hz, 1H), 8.75 (dd, J=4.7, 1.7 Hz, 1H), 9.09 (d, J=1.4 Hz, 1H) ppm; MS (DCI/NH3) m/z 282 (M+H)+, 284 (M+H)+.

Sources & evidence

ORD record
ord-97460a00d7c24a0489f610a89f4ec6dc
Source dataset
uspto-grants-2013_02
Patent number
US08383658B2

Reaction notes

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