2-Methylpyridine-4-boronic acid → HCID 58109692, compound

HRID 2037636Notes

Reaction equation

HRID 2037636 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([C@@H:8]([N:10]2[CH2:15][CH2:14][C@@:13]([C:19]3[CH:24]=[CH:23][C:22]([F:25])=[CH:21][CH:20]=3)([CH2:16][CH2:17][OH:18])[O:12][C:11]2=[O:26])[CH3:9])=[CH:4][CH:3]=1.[CH3:27][C:28]1[CH:33]=[C:32](B(O)O)[CH:31]=[CH:30][N:29]=1>>[F:25][C:22]1[CH:23]=[CH:24][C:19]([C@:13]2([CH2:16][CH2:17][OH:18])[O:12][C:11](=[O:26])[N:10]([C@H:8]([C:5]3[CH:6]=[CH:7][C:2]([C:32]4[CH:31]=[CH:30][N:29]=[C:28]([CH3:27])[CH:33]=4)=[CH:3][CH:4]=3)[CH3:9])[CH2:15][CH2:14]2)=[CH:20][CH:21]=1

Participants

3

Reactant 2

HCID 41926642-Methylpyridine-4-boronic acidHCID 58109626HCID 58109626, compound

Product 1

HCID 58109692HCID 58109692, compound

Procedure

The title compound was prepared from (S)-3-((S)-1-(4-bromophenyl)ethyl)-6-(4-fluorophenyl)-6-(2-hydroxyethyl)-1,3-oxazinan-2-one and 2-methylpyridine-4-boronic acid following a procedure analogous to that described in Example 75 Step 1. LC-MS Method 2 tR=0.945 min, m/z=435.5; 1H NMR (CD3OD) 1.56 (d, 3H), 1.92 (m, 1H), 2.01 (m, 1H), 2.17 (m, 2H), 2.36 (m, 2H), 2.48 (m, 1H), 2.56 (m, 3H), 3.12 (m, 1H), 3.62 (m, 1H), 5.62 (m, 1H), 7.05 (m, 4H), 7.30 (m, 2H), 7.44 (m, 1H), 7.54 (m, 3H), 8.39 (s, 2H).

Sources & evidence

ORD record
ord-2fd5f59426ba45f393b7dd5a14bb54cf
Source dataset
uspto-grants-2013_11
Patent number
US08575156B2

Reaction notes

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