4-[4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]pyridine → (+/-)-2-Methyl-2-(methylsulfonyl)-4-[2-oxo-4-(4-pyridin-4-ylphenyl)pyridin-1 (2H)-yl]-N-(tetrahydro-2H-pyran-2-yloxy)butanamide
Reaction equation
I[C:2]1[CH:7]=[CH:6][N:5]([CH2:8][CH2:9][C:10]([CH3:25])([S:21]([CH3:24])(=[O:23])=[O:22])[C:11]([NH:13][O:14][CH:15]2[CH2:20][CH2:19][CH2:18][CH2:17][O:16]2)=[O:12])[C:4](=[O:26])[CH:3]=1.CC1(C)C(C)(C)OB([C:35]2[CH:40]=[CH:39][C:38]([C:41]3[CH:46]=[CH:45][N:44]=[CH:43][CH:42]=3)=[CH:37][CH:36]=2)O1>>[CH3:25][C:10]([S:21]([CH3:24])(=[O:23])=[O:22])([CH2:9][CH2:8][N:5]1[CH:6]=[CH:7][C:2]([C:35]2[CH:36]=[CH:37][C:38]([C:41]3[CH:42]=[CH:43][N:44]=[CH:45][CH:46]=3)=[CH:39][CH:40]=2)=[CH:3][C:4]1=[O:26])[C:11]([NH:13][O:14][CH:15]1[CH2:20][CH2:19][CH2:18][CH2:17][O:16]1)=[O:12]Participants
3
Reactant 2
Product 1
Procedure
(+/−)-4-(4-Iodo-2-oxopyridin-1(2H)-yl)-2-methyl-2-(methylsulfonyl)-N-(tetrahydro-2H-pyran-2-yloxy)butanamide, which may be prepared as in Preparation 2A and 4-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]pyridine were converted to the title product following the general procedure outlined for (+/−)-4-[4-(1-benzofuran-2-yl)-2-oxopyridin-1(2H)-yl]-2-methyl-2-(methylsulfonyl)-N-(tetrahydro-2H-pyran-2-yloxy)butanamide in Example 33, Step A. The title compound was obtained as a white solid (161 mg, 61%) LC-MS m/z 526.7 (M+1).
Sources & evidence
- ORD record
- ord-fbf52d43dbb1444f8525357dc47444fe
- Source dataset
- uspto-grants-2015_11
- Patent number
- US09180123B2
Reaction notes
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