Ammonia → 5-(3-(Pyridin-2-yl)isoxazol-5-yl)nicotinonitrile
Reaction equation
I[C:2]1[O:6][N:5]=[C:4]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][N:8]=2)[CH:3]=1.CC1(C)C(C)(C)OB([C:21]2[CH:22]=[N:23][CH:24]=[C:25]([CH:28]=2)[C:26]#[N:27])O1.N>>[N:8]1[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=1[C:4]1[CH:3]=[C:2]([C:21]2[CH:22]=[N:23][CH:24]=[C:25]([CH:28]=2)[C:26]#[N:27])[O:6][N:5]=1Participants
4
Procedure
The titled compound was prepared as the bishydrochloride salt according to Method CC using 5-iodo-3-(pyridin-2-yl)isoxazole (136 mg, 0.5 mmol) and 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)nicotinonitrile (Frontier, 173 mg, 0.750 mmol). 1H NMR (300 MHz, DMSO-d6) δ 7.60 (ddd, J=7.3, 4.8, 1.4 Hz, 1H), 7.93 (s, 1H), 8.04 (td, J=7.6, 1.8 Hz, 1H), 8.11 (dt, J=7.9, 1.2 Hz, 1H), 8.78 (ddd, J=2.9, 1.8 Hz, 1H), 8.96 (t, J=2.2 Hz, 1H), 9.16 (d, J=1.6 Hz, 1H), 9.47 (d, J=2.0 Hz, 1H) ppm; MS (DCI/NH3) m/z 249 (M+H)+.
Sources & evidence
- ORD record
- ord-0806d5f165354607950782d57179a44e
- Source dataset
- uspto-grants-2013_02
- Patent number
- US08383658B2
Reaction notes
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