5-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)nicotinonitrile → 5-(3-(3-Amino-4-fluoro-1-(2-methoxypyridin-4-yl)-1H-isoindol-1-yl) phenyl)nicotinonitrile acetate
Reaction equation
Br[C:2]1[CH:3]=[C:4]([C:8]2([C:19]3[CH:24]=[CH:23][N:22]=[C:21]([O:25][CH3:26])[CH:20]=3)[C:16]3[C:11](=[C:12]([F:17])[CH:13]=[CH:14][CH:15]=3)[C:10]([NH2:18])=[N:9]2)[CH:5]=[CH:6][CH:7]=1.[C:27]([C:29]1[CH:30]=[N:31][CH:32]=[C:33](B2OC(C)(C)C(C)(C)[O:36]2)[CH:34]=1)#[N:28]>>[C:21]([OH:25])(=[O:36])[CH3:20].[NH2:18][C:10]1[C:11]2[C:16](=[CH:15][CH:14]=[CH:13][C:12]=2[F:17])[C:8]([C:4]2[CH:3]=[C:2]([C:33]3[CH:32]=[N:31][CH:30]=[C:29]([CH:34]=3)[C:27]#[N:28])[CH:7]=[CH:6][CH:5]=2)([C:19]2[CH:24]=[CH:23][N:22]=[C:21]([O:25][CH3:26])[CH:20]=2)[N:9]=1Participants
3
Procedure
The title compound was synthesized as described for example 27 in 52% yield, starting from 1-(3-bromophenyl)-4-fluoro-1-(2-methoxypyridin-4-yl)-1H-isoindol-3-amine (100 mg, 0.24 mmol) and 3-cyanopyridine-5-boronic acid pinacol ester (58.6 mg, 0.25 mmol). 1H NMR (400 MHz, DMSO-d6) δ ppm 9.06 (d, 1 H) 9.00 (d, 1 H) 8.56 (s, 1 H) 8.04 (d, 1 H) 7.79 (d, 1 H) 7.63-7.73 (m, 2 H) 7.51-7.60 (m, 1 H) 7.41-7.51 (m, 2 H) 7.28 (t, 1 H) 6.90 (d, 1 H) 6.64 (s, 1 H) 3.78 (s, 3 H) 1.89 (s, 3 H); MS (ES+) m/z 436 [M+H]+.
Sources & evidence
- ORD record
- ord-e9f2d14f7b354f56ad911a85d8e6dc51
- Source dataset
- uspto-grants-2011_10
- Patent number
- US08030500B2
Reaction notes
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