4-Bromo-2,6-dimethylpyridine 1-oxide → HCID 58109593, compound

HRID 1046215Notes

Reaction equation

HRID 1046215 reaction equation
[OH:1][C:2]([CH3:36])([CH3:35])[CH2:3][C@@:4]1([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[O:9][C:8](=[O:10])[N:7]([C@H:11]([C:14]2[CH:19]=[CH:18][C:17](B3OC(C)(C)C(C)(C)O3)=[CH:16][CH:15]=2)[CH2:12][CH3:13])[CH2:6][CH2:5]1.Br[C:38]1[CH:43]=[C:42]([CH3:44])[N+:41]([O-:45])=[C:40]([CH3:46])[CH:39]=1>>[OH:1][C:2]([CH3:35])([CH3:36])[CH2:3][C@@:4]1([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[O:9][C:8](=[O:10])[N:7]([C@H:11]([C:14]2[CH:15]=[CH:16][C:17]([C:38]3[CH:43]=[C:42]([CH3:44])[N+:41]([O-:45])=[C:40]([CH3:46])[CH:39]=3)=[CH:18][CH:19]=2)[CH2:12][CH3:13])[CH2:6][CH2:5]1

Participants

3

Reactant 2

HCID 124930354-Bromo-2,6-dimethylpyridine 1-oxideHCID 66600802(S)-6-(2-hydroxy-2-methylpropyl)-6-phenyl-3-((S)-1-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)propyl)-1,3-oxazinan-2-one

Product 1

HCID 58109593HCID 58109593, compound

Procedure

The title compound was prepared from (S)-6-(2-hydroxy-2-methylpropyl)-6-phenyl-3-((S)-1-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)propyl)-1,3-oxazinan-2-one and 4-bromo-2,6-dimethylpyridine-N-oxide following a procedure analogous to that described in Example 1 Step 2. LC-MS Method 2 tR=1.185 min, m/z=489.2; 1H NMR (CDCl3) 0.96 (t, 3H), 1.03 (s, 3H), 1.12 (s, 3H), 1.81-2.00 (m, 4H), 2.11-2.22 (m, 5H), 2.30-2.42 (m, 1H), 2.57 (s, 6H), 2.87 (m, 1H), 5.43 (m, 1H), 7.09 (d, 2H), 7.18 (m, 1H), 7.22 (m, 4H), 7.26 (m, 2H), 7.31 (m, 2H).

Sources & evidence

ORD record
ord-73c7bb559cea4562909f0ef67c19b01b
Source dataset
uspto-grants-2013_10
Patent number
US08569292B2

Reaction notes

Loading…