Ammonia → 5-(3-Chlorophenyl)-3-(pyridin-3-yl)isoxazole

HRID 390452Notes

Reaction equation

HRID 390452 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:17]=[CH:16][CH:15]=[C:14]([C:18]#[CH:19])[CH:13]=1.N>>[Cl:11][C:12]1[CH:13]=[C:14]([C:18]2[O:1][N:2]=[C:3]([C:4]3[CH:5]=[N:6][CH:7]=[CH:8][CH:9]=3)[CH:19]=2)[CH:15]=[CH:16][CH:17]=1

Participants

4

Reactant 3

HCID 222AmmoniaHCID 1230861-Chloro-3-ethynylbenzeneHCID 53404818N-Hydroxy-3-pyridinecarboximidoyl chloride

Product 1

HCID 445462825-(3-Chlorophenyl)-3-(pyridin-3-yl)isoxazole

Procedure

The titled compound was prepared according to Method CB using the product of Example 1A (78 mg, 0.5 mmol) and 1-chloro-3-ethynylbenzene (Apollo, 68 mg, 0.5 mmol). 1H NMR (300 MHz, MeOH-d4) δ 7.46 (s, 1H), 7.49-7.55 (m, 2 H), 7.60 (ddd, J=8.0, 4.9, 1.0 Hz, 1H), 7.82-7.90 (m, 1H), 7.93-8.00 (m, 1H), 8.37 (dt, J=7.9, 2.0 Hz, 1H), 8.67 (dd, J=5.1, 1.7 Hz, 1H), 9.09 (d, J=1.4 Hz, 1H) ppm; MS (DCI/NH3) m/z 259 (M+H)+, 257 (M+H)+.

Sources & evidence

ORD record
ord-5b9fd4ef14194f4aac6f32264ea7268a
Source dataset
uspto-grants-2013_02
Patent number
US08383658B2

Reaction notes

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