5-bromo-2-ethoxy-3-methylpyridine → HCID 58109498, compound

HRID 1046219Notes

Reaction equation

[OH:1][C:2]([CH3:35])([CH3:34])[CH2:3][C@@:4]1([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[O:9][C:8](=[O:10])[N:7]([C@H:11]([C:13]2[CH:18]=[CH:17][C:16](B3OC(C)(C)C(C)(C)O3)=[CH:15][CH:14]=2)[CH3:12])[CH2:6][CH2:5]1.Br[C:37]1[CH:38]=[C:39]([CH3:46])[C:40]([O:43][CH2:44][CH3:45])=[N:41][CH:42]=1>>[CH2:44]([O:43][C:40]1[N:41]=[CH:42][C:37]([C:16]2[CH:15]=[CH:14][C:13]([C@@H:11]([N:7]3[CH2:6][CH2:5][C@:4]([CH2:3][C:2]([OH:1])([CH3:34])[CH3:35])([C:28]4[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=4)[O:9][C:8]3=[O:10])[CH3:12])=[CH:18][CH:17]=2)=[CH:38][C:39]=1[CH3:46])[CH3:45]

Participants

Reactant 2

HCID 47384795-bromo-2-ethoxy-3-methylpyridine

HCID 59532385(S)-6-(2-hydroxy-2-methylpropyl)-6-phenyl-3-((S)-1-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)ethyl)-1,3-oxazinan-2-one

Product 1

HCID 58109498HCID 58109498, 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)ethyl)-1,3-oxazinan-2-one and 5-bromo-2-ethoxy-3-methylpyridine following a procedure analogous to that described in Example 1 Step 2. LC-MS Method 2 tR=1.314 min, m/z=489; 1H NMR (CDCl3) 1.04 (s, 3H), 1.11 (s, 3H), 1.34 (t, 3H), 1.47 (d, 3H), 2.13-2.24 (m, 7H), 2.32 (m, 1H), 2.81 (m, 1H), 4.34 (q, 2H), 5.62 (q, 1H), 6.93 (d, 2H), 7.17-7.27 (m, 7H), 7.42 (s, 1H), 8.02 (s, 1H).

Sources & evidence

ORD record: ord-3e76a3b23b1b4ab58c6d94c2c655c37c
Source dataset: uspto-grants-2013_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08569292B2

Reaction notes

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