Sodium Carbonate → (S)-5,5-dimethyl-3-(4-(2-oxo-1,2-dihydropyridin-3-yl)phenyl)-4-phenyloxazolidin-2-one

HRID 525401Notes

Reaction equation

HRID 525401 reaction equation
[CH3:1][C:2]1([CH3:29])[O:6][C:5](=[O:7])[N:4]([C:8]2[CH:13]=[CH:12][C:11](B3OC(C)(C)C(C)(C)O3)=[CH:10][CH:9]=2)[C@H:3]1[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.Br[C:31]1[CH:32]=[C:33](I)[C:34](=[O:37])[NH:35][CH:36]=1.C(=O)([O-])[O-].[Na+].[Na+].O1CCOCC1>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.O>[CH3:1][C:2]1([CH3:29])[O:6][C:5](=[O:7])[N:4]([C:8]2[CH:13]=[CH:12][C:11]([C:33]3[C:34](=[O:37])[NH:35][CH:36]=[CH:31][CH:32]=3)=[CH:10][CH:9]=2)[C@H:3]1[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Participants

7

Reactant 4

HCID 10340Sodium CarbonateHCID 312751,4-DioxaneHCID 120277875-Bromo-3-iodopyridin-2-olHCID 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 89814341(S)-5,5-dimethyl-3-(4-(2-oxo-1,2-dihydropyridin-3-yl)phenyl)-4-phenyloxazolidin-2-oneYield 23%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

A resealable tube was charged with (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)(0.100 g, 0.254 mmol), 5-bromo-3-iodopyridin-2(1H)-one (commercially available from Adesis, Inc., New Castle, Del.)(0.153 g, 0.509 mmol), sodium carbonate (0.108 g, 1.017 mmol), dioxane (2.0 mL), and water (0.40 mL). Tetrakis(triphenylphosphine)palladium(0) (0.147 g, 0.127 mmol) was added, the system was purged with argon, and the tube was sealed. The mixture was then stirred at 100° C. for 16 hours. The reaction mixture was filtered through Celite® brand filter aid. The filtrate was then concentrated to afford a black oil. The oil thus obtained was purified using column chromatography on silica gel (RediSep 40 g column, gradient elution with 0-100% EtOAc-hexane) to afford (S)-5,5-dimethyl-3-(4-(2-oxo-1,2-dihydropyridin-3-yl)phenyl)-4-phenyloxazolidin-2-one (0.021 g, 0.058 mmol, 23% yield) as an off-white solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 0.91 (s, 3H), 1.64 (s, 3H), 5.46 (s, 1H), 6.24 (t, J=6.70 Hz, 1H), 7.20-7.43 (m, 6H), 7.48 (d, J=8.90 Hz, 2H), 7.58 (dd, J=6.94, 2.05 Hz, 1H), 7.65 (d, J=8.80 Hz, 2H), 11.72 (br. s., 1H). m/z (ESI) 361 (M+H)+.

Workup

  1. customthe system was purged with argon
  2. customthe tube was sealed
  3. filtrationThe reaction mixture was filtered through Celite® brand
  4. filtrationfilter aid
  5. concentrationThe filtrate was then concentrated
  6. customto afford a black oil
  7. customThe oil thus obtained
  8. customwas purified

Sources & evidence

ORD record
ord-e0360febc3ad49bba5c7adbadedb9f8e
Source dataset
uspto-grants-2016_05
Patent number
US09340549B2

Reaction notes

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