2-Bromo-5-fluoropyridine → HCID 44625911, compound

HRID 1046197Notes

Reaction equation

HRID 1046197 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:42]=[CH:41][C:40]([F:43])=[CH:39][N:38]=1>C(OCC)(=O)C>[F:43][C:40]1[CH:41]=[CH:42][C:37]([C:16]2[CH:17]=[CH:18][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:29]=[CH:30][CH:31]=[CH:32][CH:33]=4)[O:9][C:8]3=[O:10])[CH3:12])=[CH:14][CH:15]=2)=[N:38][CH:39]=1

Participants

4

Reactant 2

HCID 27831712-Bromo-5-fluoropyridineHCID 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 44625911HCID 44625911, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

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 2-bromo-5-fluoropyridine following a procedure analogous to that described in Example 1 Step 2. LC-MS Method 2 tR=1.363, m/z=390.9; 1H NMR (CDCl3) 1.11 (s, 3H), 1.19 (s, 3H), 1.53 (d, 3H), 2.16-2.30 (m, 4H), 2.32-2.43 (m, 1H), 2.86 (m, 1H), 5.71 (m, 1H), 7.03 (d, 2H), 7.30 (m, 1H), 7.36 (m, 4H), 7.44 (m, 1H), 7.69 (dd, 1H), 7.68 (d, 2H), 8.43 (d, 1H). The compound was dissolved in refluxing ethyl acetate and allowed to cool slowly to rt to afford a solid with mp 159-160° C.

Workup

  1. dissolutionThe compound was dissolved
  2. customto afford a solid with mp 159-160° C.

Sources & evidence

ORD record
ord-9076e5ffcf95464f9b3c7c32f148f711
Source dataset
uspto-grants-2013_10
Patent number
US08569292B2

Reaction notes

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