Sodium Carbonate → HCID 89813921, compound

HRID 525412Notes

Reaction equation

FC(F)(F)S(O[C:7]1[CH2:12][CH2:11][C@H:10]([N:13]2[C@@H:17]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[C:16]([CH3:25])([CH3:24])[O:15][C:14]2=[O:26])[CH2:9][CH:8]=1)(=O)=O.CC1(C)C(C)(C)OB([C:37]2[CH:38]=[N:39][CH:40]=[CH:41][CH:42]=2)O1.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>[CH3:24][C:16]1([CH3:25])[O:15][C:14](=[O:26])[N:13]([C@H:10]2[CH2:11][CH2:12][C:7]([C:37]3[CH:38]=[N:39][CH:40]=[CH:41][CH:42]=3)=[CH:8][CH2:9]2)[C@H:17]1[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

Conditions

Temperature: 100 °C

Procedure

A microwave tube was charged with (S)-4-((S)-5,5-dimethyl-2-oxo-4-phenyloxazolidin-3-yl)cyclohex-1-en-1-yl trifluoromethanesulfonate (0.205 g, 0.489 mmol), 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine (0.120 g, 0.587 mmol), tetrakis(triphenylphosphine)palladium(0) (0.085 g, 0.073 mmol) and sodium carbonate (0.155 g, 1.466 mmol). Dioxane (1.70 mL) and water (0.25 mL) were added and the vial was charged with argon. The reaction mixture was heated to 100° C. with microwave for 1 h. The reaction mixture was purified via column chromatography on silica gel (RediSep 12 g column, gradient elution with 0% to 50% (90:10 CH2Cl2—MeOH—CH2Cl2) to afford (S)-5,5-dimethyl-4-phenyl-3-((S)-4-(pyridin-3-yl)cyclohex-3-en-1-yl)oxazolidin-2-one (0.128 g, 0.367 mmol, 75% yield) as a yellow oil.

Workup

additionthe vial was charged with argon
customThe reaction mixture was purified via column chromatography on silica gel (
washRediSep 12 g column, gradient elution with 0% to 50% (90:10 CH2Cl2—MeOH—CH2Cl2)

Sources & evidence

ORD record: ord-110ee16a32444c47bad5b508f1a55e6d
Source dataset: uspto-grants-2016_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09340549B2

Reaction notes

Loading…