Sodium Carbonate → HCID 89813788, compound

HRID 525397Notes

Reaction equation

HRID 525397 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5](Br)=[CH:4][N:3]=1.C(=O)([O-])[O-].[Na+].[Na+].[CH3:15][C:16]1([CH3:43])[O:20][C:19](=[O:21])[N:18]([C:22]2[CH:27]=[CH:26][C:25](B3OC(C)(C)C(C)(C)O3)=[CH:24][CH:23]=2)[C@H:17]1[C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1>O1CCOCC1>[NH2:1][C:2]1[N:3]=[CH:4][C:5]([C:25]2[CH:24]=[CH:23][C:22]([N:18]3[C@@H:17]([C:37]4[CH:38]=[CH:39][CH:40]=[CH:41][CH:42]=4)[C:16]([CH3:15])([CH3:43])[O:20][C:19]3=[O:21])=[CH:27][CH:26]=2)=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 706222-Amino-5-bromopyridineHCID 89813960(S)-5,5-dimethyl-4-phenyl-3-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)oxazolidin-2-one2×

Product 1

HCID 89813788HCID 89813788, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
115 °C

Procedure

2-Amino-5-bromopyridine (commercially available from Sigma-Aldrich, Milwaukee, Wis.)(0.114 mL, 5.09 mmol), sodium carbonate (5.09 mL, 10.17 mmol), (S)-5,5-dimethyl-4-phenyl-3-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)oxazolidin-2-one (Intermediate J)(2.0 g, 5.09 mmol), and dichloro(1,1-bis(diphenylphosphinoferrocene))palladium(II) (415 mg, 0.509 mmol) were combined in dioxane (10.200 mL) and stirred at 115° C. overnight. LC-MS indicated good conversion to desired product. After cooling to room temperature, the reaction mixture was absorbed onto a plug of silica gel and purified by chromatography through a Redi-Sep pre-packed silica gel column (12 g), eluting with a gradient of 0% to 100% EtOAc in hexane, to provide (S)-3-(4-(6-aminopyridin-3-yl)phenyl)-5,5-dimethyl-4-phenyloxazolidin-2-one (1 g, 2.78 mmol, 54.7% yield) as an off-white solid. m/z (ESI) 360.0 (M+H)+.

Sources & evidence

ORD record
ord-d317fd2989b1423da008e44ec7eb5417
Source dataset
uspto-grants-2016_05
Patent number
US09340549B2

Reaction notes

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