Ammonia → 5-(3,5-Difluorophenyl)-3-(pyrimidin-5-yl)isoxazole

HRID 390481Notes

Reaction equation

HRID 390481 reaction equation
[OH:1][N:2]=[C:3](Cl)[C:4]1[CH:5]=[N:6][CH:7]=[N:8][CH:9]=1.[C:11]([C:13]1[CH:18]=[C:17]([F:19])[CH:16]=[C:15]([F:20])[CH:14]=1)#[CH:12].N>>[F:19][C:17]1[CH:18]=[C:13]([C:11]2[O:1][N:2]=[C:3]([C:4]3[CH:5]=[N:6][CH:7]=[N:8][CH:9]=3)[CH:12]=2)[CH:14]=[C:15]([F:20])[CH:16]=1

Participants

4

Reactant 3

HCID 222AmmoniaHCID 42068061-Ethynyl-3,5-difluorobenzeneHCID 86636847N-Hydroxypyrimidine-5-carbimidoyl chloride

Product 1

HCID 445464205-(3,5-Difluorophenyl)-3-(pyrimidin-5-yl)isoxazole

Procedure

The titled compound was prepared as the hydrochloride salt according to Method CB using the product of Example 44B (79 mg, 0.5 mmol) and 1-ethynyl-3,5-difluorobenzene (Apollo, 69 mg, 0.5 mmol). 1H NMR (300 MHz, DMSO-d6) δ 7.52 (tt, J=9.5, 2.4 Hz, 1H), 7.62-7.78 (m, 2H), 7.93 (s, 1H), 9.30 (s, 2H), 9.36 (s, 1H) ppm; MS (DCI/NH3) m/z 260 (M+H)+.

Sources & evidence

ORD record
ord-848522a5605549cd8986f7bb3edcfadb
Source dataset
uspto-grants-2013_02
Patent number
US08383658B2

Reaction notes

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