4-(Hydroxymethyl)benzeneboronic acid → 4-(2,3-Dimethylphenoxy)-1-(5-(1-((2-(methylthio)pyrimidin-4-yl)methyl)-1H-pyrazol-4-yl)-3,4-dihydroquinolin-1(2H)-yl)butan-1-one
Reaction equation
[CH3:1][C:2]1[C:31]([CH3:32])=[CH:30][CH:29]=[CH:28][C:3]=1[O:4][CH2:5][CH2:6][CH2:7][C:8]([N:10]1[C:19]2[C:14](=[C:15](C3C=CC(CO)=CC=3)[CH:16]=[CH:17][CH:18]=2)[CH2:13][CH2:12][CH2:11]1)=[O:9].OCC1C=CC(B(O)O)=CC=1.[CH3:44][S:45][C:46]1[N:51]=[C:50]([CH2:52][N:53]2[CH:57]=[C:56](B3OC(C)(C)C(C)(C)O3)[CH:55]=[N:54]2)[CH:49]=[CH:48][N:47]=1>>[CH3:1][C:2]1[C:31]([CH3:32])=[CH:30][CH:29]=[CH:28][C:3]=1[O:4][CH2:5][CH2:6][CH2:7][C:8]([N:10]1[C:19]2[C:14](=[C:15]([C:56]3[CH:55]=[N:54][N:53]([CH2:52][C:50]4[CH:49]=[CH:48][N:47]=[C:46]([S:45][CH3:44])[N:51]=4)[CH:57]=3)[CH:16]=[CH:17][CH:18]=2)[CH2:13][CH2:12][CH2:11]1)=[O:9]Participants
4
Reactant 3
Product 1
Procedure
The title compound was prepared using a procedure analogous to 4-(2,3-dimethylphenoxy)-1-(5-(4-(hydroxymethyl)phenyl)-3,4-dihydroquinolin-1(2H)-yl)butan-1-one except that 4-(hydroxymethyl)phenylboronic acid was replaced with 2-(methylthio)-4-((4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl)methyl)pyrimidine. LCMS, [M+H]+=528.4. 1H NMR (400 MHz, CDCl3) δ 8.51 (d, J=5.3 Hz, 1H), 7.62 (s, 1H), 7.46 (s, 1H), 7.16-7.25 (m, 3H), 7.02 (t, J=7.8 Hz, 1H), 6.74 (d, J=7.5 Hz, 1H), 6.69 (d, J=5.1 Hz, 1H), 6.65 (d, J=8.4 Hz, 1H), 5.40 (s, 2H), 3.94 (t, J=5.5 Hz, 2H), 3.81 (t, J=6.8 Hz, 2H), 2.79 (t, J=7.2 Hz, 2H), 2.54-2.63 (m, 5H), 2.11-2.26 (m, 5H), 1.82-1.97 (m, 5H).
Sources & evidence
- ORD record
- ord-06c4bbf9ee2e460ab4511622cdd501f0
- Source dataset
- uspto-grants-2015_06
- Patent number
- US09062028B2
Reaction notes
Loading…