Sodium Carbonate → 1-((4'-Butoxy(1,1'-biphenyl)-4-yl)thio)-3-(4,4-dimethyl-2,5-dioxoimidazolidin-1-yl)-2-propanone

HRID 1978025Notes

Reaction equation

Br[C:2]1[CH:7]=[CH:6][C:5]([S:8][CH2:9][C:10](=[O:21])[CH2:11][N:12]2[C:16](=[O:17])[C:15]([CH3:19])([CH3:18])[NH:14][C:13]2=[O:20])=[CH:4][CH:3]=1.[CH2:22]([O:26][C:27]1[CH:32]=[CH:31][C:30](B(O)O)=[CH:29][CH:28]=1)[CH2:23][CH2:24][CH3:25].C(=O)([O-])[O-].[Na+].[Na+]>COCCOC.C(OCC)(=O)C.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[CH2:22]([O:26][C:27]1[CH:32]=[CH:31][C:30]([C:2]2[CH:7]=[CH:6][C:5]([S:8][CH2:9][C:10](=[O:21])[CH2:11][N:12]3[C:16](=[O:17])[C:15]([CH3:19])([CH3:18])[NH:14][C:13]3=[O:20])=[CH:4][CH:3]=2)=[CH:29][CH:28]=1)[CH2:23][CH2:24][CH3:25]

Participants

Conditions

Temperature: 90 °C

Procedure

A solution of Example 46A (700 mg, 1.89 mmol) in DME (20 mL) at room temperature was treated with 4-n-butoxybenzeneboronic acid (549 mg, 2.83 mmol), tetrakis-(triphenylphosphine)-palladium (218 mg, 0.189 mmol) and 1M sodium carbonate (3.54 mL, 3.54 mmol), the reaction vessel was sealed and heated at 90° C. for 6 hours, diluted with ethyl acetate, washed with sequentially saturated ammonium chloride solution, water and brine, dried (Na2SO4), filtered, concentrated and purified on silica gel with 30 to 50% ethyl acetate/dichloromethane to provide 650 mg (78%) of the desired product as a yellow solid.

Workup

customthe reaction vessel was sealed
washwashed with sequentially saturated ammonium chloride solution, water and brine
dry with materialdried (Na2SO4)
filtrationfiltered
concentrationconcentrated
custompurified on silica gel with 30 to 50% ethyl acetate/dichloromethane

Sources & evidence

ORD record: ord-89b45d9ae1264a8bb277584400006a80
Source dataset: uspto-grants-2001_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06235786B1

Reaction notes

Loading…