Ammonia → 2-Fluoro-5-(3-(pyridin-3-yl)isoxazol-5-yl)benzonitrile

HRID 390500Notes

Reaction equation

HRID 390500 reaction equation
[OH:1][N:2]=[C:3](Cl)[C:4]1[CH:9]=[CH:8][CH:7]=[N:6][CH:5]=1.[C:11]([C:13]1[CH:14]=[CH:15][C:16]([F:21])=[C:17]([CH:20]=1)[C:18]#[N:19])#[CH:12].N>>[F:21][C:16]1[CH:15]=[CH:14][C:13]([C:11]2[O:1][N:2]=[C:3]([C:4]3[CH:5]=[N:6][CH:7]=[CH:8][CH:9]=3)[CH:12]=2)=[CH:20][C:17]=1[C:18]#[N:19]

Participants

4

Reactant 3

HCID 222AmmoniaHCID 53404818N-Hydroxy-3-pyridinecarboximidoyl chlorideHCID 534292955-Ethynyl-2-fluorobenzonitrile

Product 1

HCID 445465472-Fluoro-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 68A (73 mg, 0.5 mmol). 1H NMR (300 MHz, MeOH-d4) δ 7.49 (s, 1H), 7.52-7.68 (m, 2H), 8.28 (ddd, J=8.8, 5.1, 2.4 Hz, 1H), 8.33-8.41 (m, 2H), 8.68 (dd, J=4.9, 1.5 Hz, 1H), 9.09 (d, J=2.4 Hz, 1H) ppm; MS (DCI/NH3) m/z 266 (M+H)+.

Sources & evidence

ORD record
ord-8dddfa36a97348dfb12af912ab9649d1
Source dataset
uspto-grants-2013_02
Patent number
US08383658B2

Reaction notes

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