4-Bromo-2,6-dimethylpyridine → HCID 58109712, compound

HRID 1046193Notes

Reaction equation

[OH:1][CH2:2][CH2:3][CH2:4][C@@:5]1([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[O:10][C:9](=[O:11])[N:8]([C@H:12]([C:14]2[CH:19]=[CH:18][C:17](B3OC(C)(C)C(C)(C)O3)=[CH:16][CH:15]=2)[CH3:13])[CH2:7][CH2:6]1.Br[C:36]1[CH:41]=[C:40]([CH3:42])[N:39]=[C:38]([CH3:43])[CH:37]=1>>[CH3:42][C:40]1[CH:41]=[C:36]([C:17]2[CH:16]=[CH:15][C:14]([C@@H:12]([N:8]3[CH2:7][CH2:6][C@:5]([CH2:4][CH2:3][CH2:2][OH:1])([C:29]4[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=4)[O:10][C:9]3=[O:11])[CH3:13])=[CH:19][CH:18]=2)[CH:37]=[C:38]([CH3:43])[N:39]=1

Participants

Reactant 2

HCID 130817354-Bromo-2,6-dimethylpyridine

HCID 59635633(R)-6-(3-hydroxypropyl)-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 58109712HCID 58109712, compound

Procedure

The title compound was prepared from (R)-6-(3-hydroxypropyl)-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 4-bromo-2,6-dimethylpyridine following a procedure analogous to that described in Example 1 Step 2. LC-MS Method 2 tR=1.228, m/z=445; 1H NMR (CDCl3) 1.32 (m, 1H) 1.51 (d, 3H), 1.60-1.72 (m, 1H), 1.86-2.02 (m, 2H), 2.19 (m, 1H), 2.25-2.39 (m, 2H), 2.79 (s, 6H), 2.93 (m, 1H), 3.50 (t, 2H), 5.64 (m, 1H), 7.00 (d, 2H), 7.21 (m, 2H), 7.29 (m, 2H), 7.32 (m, 3H), 7.40 (m, 2H).

Sources & evidence

ORD record: ord-5dda797db06e4d678d19a4f0ae2e01a1
Source dataset: uspto-grants-2013_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08569292B2

Reaction notes

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