(6-Bromopyridin-2-yl)-(4-methylpyridin-2-yl)amine → 4-(5-(6-(4-Methylpyridin-2-ylamino)pyridin-2-yl)thiazol-2-yl)benzonitrile
Reaction equation
Br[C:2]1[N:7]=[C:6]([NH:8][C:9]2[CH:14]=[C:13]([CH3:15])[CH:12]=[CH:11][N:10]=2)[CH:5]=[CH:4][CH:3]=1.C([Sn](CCCC)(CCCC)[C:21]1[S:25][C:24]([C:26]2[CH:33]=[CH:32][C:29]([C:30]#[N:31])=[CH:28][CH:27]=2)=[N:23][CH:22]=1)CCC>>[CH3:15][C:13]1[CH:12]=[CH:11][N:10]=[C:9]([NH:8][C:6]2[N:7]=[C:2]([C:21]3[S:25][C:24]([C:26]4[CH:27]=[CH:28][C:29]([C:30]#[N:31])=[CH:32][CH:33]=4)=[N:23][CH:22]=3)[CH:3]=[CH:4][CH:5]=2)[CH:14]=1Participants
3
Procedure
By following essentially the same procedure in preparative example 020 and starting with 6-bromo-N-(4-methylpyridin-2-yl)pyridin-2-amine (100 mg 0.38 mmol) and 4-(5-(tributylstannyl)thiazol-2-yl)benzonitrile (328 mg, 0.69 mmol), the 4-(5-(6-(4-methylpyridin-2-ylamino)pyridin-2-yl)thiazol-2-yl)benzonitrile was obtained and purified by dry flash chromatography over SiO2 eluting with EtOAc/Cyclohexane 50/50-MeOH (5%) and by trituration with Et2O (51 mg, 37%). 1H NMR (300 MHz, DMSO-d6) δ 9.77 (br s, 1H), 8.65 (s, 1H), 8.20-8.10 (m, 3H), 8.00 (d, J=8.4 Hz, 2H), 7.93 (br s, 1H), 7.75 (t, J=7.9 Hz, 1H), 7.55 (d, J=7.4 Hz, 1H), 7.50 (d, J=8.3 Hz, 1H), 6.80 (d, J=5.1 Hz, 1H), 2.39 (s, 3H). (APCI+) m/z 370 (M+H)+.
Sources & evidence
- ORD record
- ord-4081c40e4582444ebb617b5a673546f8
- Source dataset
- uspto-grants-2015_02
- Patent number
- US08962665B2
Reaction notes
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