Sodium Carbonate → (4S)-5,5-dimethyl-3-(4-(2-oxo-1,2-dihydro-1,7-naphthyridin-3-yl)cyclohex-3-en-1-yl)-4-phenyloxazolidin-2-one

HRID 525414Notes

Reaction equation

HRID 525414 reaction equation
[CH3:1][C:2]1([CH3:29])[O:6][C:5](=[O:7])[N:4]([CH:8]2[CH2:13][CH2:12][C:11](B3OC(C)(C)C(C)(C)O3)=[CH:10][CH2:9]2)[C@H:3]1[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.Br[C:31]1[C:32](=[O:41])[NH:33][C:34]2[C:39]([CH:40]=1)=[CH:38][CH:37]=[N:36][CH:35]=2.C(=O)([O-])[O-].[Na+].[Na+].O1CCOCC1>C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2].O>[CH3:1][C:2]1([CH3:29])[O:6][C:5](=[O:7])[N:4]([CH:8]2[CH2:13][CH2:12][C:11]([C:31]3[C:32](=[O:41])[NH:33][C:34]4[C:39]([CH:40]=3)=[CH:38][CH:37]=[N:36][CH:35]=4)=[CH:10][CH2:9]2)[C@H:3]1[C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1

Participants

7

Reactant 4

HCID 10340Sodium CarbonateHCID 312751,4-DioxaneHCID 89813616(4S)-5,5-dimethyl-4-phenyl-3-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)cyclohex-3-en-1-yl)oxazolidin-2-oneHCID 89815694HCID 89815694, compound

Product 1

HCID 89813573(4S)-5,5-dimethyl-3-(4-(2-oxo-1,2-dihydro-1,7-naphthyridin-3-yl)cyclohex-3-en-1-yl)-4-phenyloxazolidin-2-oneYield 38.6%

Reagents, catalysts & solvents 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

A microwave vial was charged with (4S)-5,5-dimethyl-4-phenyl-3-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)cyclohex-3-en-1-yl)oxazolidin-2-one (0.124 g, 0.312 mmol), 3-bromo-1,7-naphthyridin-2(1H)-one (0.105 g, 0.468 mmol), sodium carbonate (0.099 g, 0.936 mmol), dioxane (3.0 mL), and water (0.600 mL). Dichloro[1,1′-bis(diphenylphosphino)ferrocene]palladium (II) dichloromethane adduct (0.026 g, 0.031 mmol) was added, the system was purged with argon, and the tube was sealed. The mixture stirred at 100° C. in the microwave for 1.5 h. The reaction mixture was filtered through Celite® brand filter aid and the filtrate was concentrated to afford a brown oil. This oil was purified via column chromatography on silica gel (RediSep 40 g column, gradient elution with 0-10% methanol-ethyl acetate) to afford (4S)-5,5-dimethyl-3-(4-(2-oxo-1,2-dihydro-1,7-naphthyridin-3-yl)cyclohex-3-en-1-yl)-4-phenyloxazolidin-2-one (0.050 g, 38.6% yield) as an off-white solid.

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 concentrated
  6. customto afford a brown oil
  7. customThis oil was purified via column chromatography on silica gel (RediSep 40 g column, gradient elution with 0-10% methanol-ethyl acetate)

Sources & evidence

ORD record
ord-ea61603a40744fedb6ffb5968977f551
Source dataset
uspto-grants-2016_05
Patent number
US09340549B2

Reaction notes

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