N-bromobutanimide → (S)-3-(4-(6-Amino-5-bromopyridin-3-yl)phenyl)-5,5-dimethyl-4-phenyloxazolidin-2-one

HRID 525398Notes

Reaction equation

HRID 525398 reaction equation
[NH2:1][C:2]1[N:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][C:11]([N:14]3[C@@H:18]([C:19]4[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=4)[C:17]([CH3:26])([CH3:25])[O:16][C:15]3=[O:27])=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.C1C(=O)N([Br:35])C(=O)C1>C(Cl)Cl>[NH2:1][C:2]1[N:7]=[CH:6][C:5]([C:8]2[CH:9]=[CH:10][C:11]([N:14]3[C@@H:18]([C:19]4[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=4)[C:17]([CH3:25])([CH3:26])[O:16][C:15]3=[O:27])=[CH:12][CH:13]=2)=[CH:4][C:3]=1[Br:35]

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 89813788HCID 89813788, compound

Product 1

HCID 89813808(S)-3-(4-(6-Amino-5-bromopyridin-3-yl)phenyl)-5,5-dimethyl-4-phenyloxazolidin-2-one

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (S)-3-(4-(6-aminopyridin-3-yl)phenyl)-5,5-dimethyl-4-phenyloxazolidin-2-one (1 g, 2.78 mmol) in DCM (13.91 mL) at 0° C., was added NBS (0.545 g, 3.06 mmol). The reaction mixture was then stirred for 1 hour at the same temperature. LC-MS indicated clean and complete conversion to desired product. The solution was concentrated and water was added. The solid was filtered and washed with water three times. The solid was then air-dried affording (S)-3-(4-(6-amino-5-bromopyridin-3-yl)phenyl)-5,5-dimethyl-4-phenyloxazolidin-2-one (1.26 g, 2.87 mmol, 103% yield) as a tan solid. The material was used without further purification. m/z (ESI) 439.8 (M+2)+.

Sources & evidence

ORD record
ord-50ca343190e5441a88125ca23eff0373
Source dataset
uspto-grants-2016_05
Patent number
US09340549B2

Reaction notes

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