Cesium carbonate → HCID 59239861, compound

HRID 1668373Notes

Reaction equation

Br[C:2]1[CH:12]=[CH:11][C:5]([C:6]([O:8][CH2:9][CH3:10])=[O:7])=[CH:4][CH:3]=1.[NH:13]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[NH2:14].C(=O)([O-])[O-].[Cs+].[Cs+]>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].C1(P(C2C=CC=CC=2)[C-]2C=CC=C2)C=CC=CC=1.[C-]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C1.[Fe+2].C1(C)C=CC=CC=1>[CH2:9]([O:8][C:6]([C:5]1[CH:11]=[CH:12][C:2]([N:13]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[NH2:14])=[CH:3][CH:4]=1)=[O:7])[CH3:10]

Participants

Conditions

Temperature: 100 °C

Procedure

Ethyl 4-bromobenzoate (25.0 g), tert-butyl hydrazinecarboxylate (28.8 g), tris(dibenzylideneacetone)dipalladium(0) (1.00 g), 1,1′-bis(diphenylphosphino)ferrocene (1.82 g) and cesium carbonate (35.6 g) were added to toluene (220 ml) under an argon atmosphere, and the mixture was stirred at 100° C. for 18 hr. The reaction mixture was filtered through celite, and the residue was washed with dichloromethane. The filtrate was concentrated under reduced pressure and the residue was purified by silica gel column chromatography (hexane:ethyl acetate=4:1, volume ratio) to give the title compound (29.9 g). A part of the compound was recrystallized from ethyl acetate-diisopropyl ether to give a colorless crystal.

Workup

filtrationThe reaction mixture was filtered through celite
washthe residue was washed with dichloromethane
concentrationThe filtrate was concentrated under reduced pressure
customthe residue was purified by silica gel column chromatography (hexane:ethyl acetate=4:1, volume ratio)

Sources & evidence

ORD record: ord-4c9a1ae2387f44929b8b5561e0095333
Source dataset: uspto-grants-2011_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07989445B2

Reaction notes

Loading…