Cesium carbonate → HCID 59631406, compound

HRID 1618773Notes

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(=C(P(C3C=CC=CC=3)C3C=CC=CC=3)C=CC=2)OC2C(P(C3C=CC=CC=3)C3C=CC=CC=3)=CC=CC1=2.[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

2,4-Dichloro-5,7-difluoro-3-methylquinoline (1.90 g, 7.70 mmol), XantPhos™ (670 mg, 1.20 mmol), azetidin-2-one (550 mg, 7.70 mmol), cesium carbonate (3.50 g, 11.0 mmol), 3 A activated molecular sieves (1.0 g) and Pd2(dba)3 (350 mg, 0.39 mmol) were slurried in 1,4-dioxane (26 mL). The reaction was heated in an oil bath at 100° C. for 3 h. After this time the reaction was cooled to rt, diluted with EtOAc and filtered over a pad of Celite™. The filtrate was concentrated and the residue was purified by column 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

temperatureAfter this time the reaction was cooled to rt
filtrationfiltered over a pad of Celite™
concentrationThe filtrate was concentrated
customthe residue was purified by column chromatography (silica gel, 0 to 30% EtOAc:DCM)

Sources & evidence

ORD record: ord-652311d913fa42db8eb3b6821e0fdf95
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08765940B2

Reaction notes

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