Cesium carbonate → HCID 59631406, compound

HRID 1431695Notes

Reaction equation

Cl[C:2]1[C:11]([CH3:12])=[C:10]([Cl:13])[C:9]2[C:4](=[CH:5][C:6]([F:15])=[CH:7][C:8]=2[F:14])[N:3]=1.CC1(C)C2C=CC=C(P(C3C=CC=CC=3)C3C=CC=CC=3)C=2OC2C1=CC=CC=2P(C1C=CC=CC=1)C1C=CC=CC=1.[NH:58]1[CH2:61][CH2:60][C:59]1=[O:62].C(=O)([O-])[O-].[Cs+].[Cs+]>O1CCOCC1.CCOC(C)=O.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]>[Cl:13][C:10]1[C:9]2[C:4](=[CH:5][C:6]([F:15])=[CH:7][C:8]=2[F:14])[N:3]=[C:2]([N:58]2[CH2:61][CH2:60][C:59]2=[O:62])[C:11]=1[CH3:12]

Participants

Conditions

Temperature: 100 °C

Procedure

The 2,4-dichloro-5,7-difluoro-3-methylquinoline (1.90 g, 7.70 mmol), (9,9-dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphine) (XantPhos) (670 mg, 1.20 mmol), azetidin-2-one (550 mg, 7.70 mmol), cesium carbonate (3.50 g, 11.0 mmol) and Pd2(dba)3 (350 mg, 0.39 mmol) were slurried in 26 mL of dry dioxane along with 1.0 grams of activated 3 A molecular sieves. The reaction was heated in an oil bath at 100° C. for 3 h. The reaction was then cooled to rt, diluted with EtOAc and filtered over a pad of celite. The filtrate was cond and the residue was purified by medium pressure chromatography (silica gel, 0 to 30% EtOAc:DCM) to give 1-(4-chloro-5,7-difluoro-3-methylquinolin-2-yl)azetidin-2-one. Mass Spectrum (ESI) m/e=283.1 (M+1).

Workup

temperatureThe reaction was then cooled to rt
filtrationfiltered over a pad of celite
customthe residue was purified by medium pressure chromatography (silica gel, 0 to 30% EtOAc:DCM)

Sources & evidence

ORD record: ord-72706c3e51ec4f99a97d7c2fa2a3105f
Source dataset: uspto-grants-2015_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08940724B2

Reaction notes

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