Ammonia → 5-(2-Chlorophenyl)-3-(pyridin-3-yl)isoxazole

HRID 390455Notes

Reaction equation

HRID 390455 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]=[CH:14][C:13]=1[C:18]#[CH:19].N>>[Cl:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[C:18]1[O:1][N:2]=[C:3]([C:4]2[CH:5]=[N:6][CH:7]=[CH:8][CH:9]=2)[CH:19]=1

Participants

4

Reactant 3

HCID 222AmmoniaHCID 5859951-Chloro-2-ethynylbenzeneHCID 53404818N-Hydroxy-3-pyridinecarboximidoyl chloride

Product 1

HCID 445462845-(2-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-2-ethynylbenzene (Apollo, 68 mg, 0.5 mmol). 1H NMR (300 MHz, MeOH-d4) δ 7.43-7.56 (m, 3H), 7.56-7.70 (m, 2H), 7.98 (dd, J=5.9, 3.6 Hz, 1H), 8.39 (dt, J=7.9, 2.0 Hz, 1H), 8.67 (dd, J=4.8, 1.6 Hz, 1H), 9.12 (d, J=2.4 Hz, 1H) ppm; MS (DCI/NH3) m/z 259 (M+H)+, 257 (M+H)+.

Sources & evidence

ORD record
ord-3767e57ce0f84e73ba8aca14ad3974c2
Source dataset
uspto-grants-2013_02
Patent number
US08383658B2

Reaction notes

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