Cesium carbonate → HCID 59631088, compound

HRID 1431693Notes

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.[CH3:58][C:59]1([CH3:65])[CH2:63][NH:62][C:61](=[O:64])[CH2:60]1.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:62]2[CH2:63][C:59]([CH3:65])([CH3:58])[CH2:60][C:61]2=[O:64])[C:11]=1[CH3:12]

Participants

Conditions

Temperature: 100 °C

Procedure

The 2,4-dichloro-5,7-difluoro-3-methylquinoline (1.50 g, 6.20 mmol), (9,9-dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphine) (XantPhos) (540 mg, 0.93 mmol), 4,4-dimethylpyrrolidin-2-one (700 mg, 6.20 mmol), cesium carbonate (2.80 g, 8.70 mmol) and Pd2(dba)3 (280 mg, 0.31 mmol) were slurried in 21 mL of dry 1,4-dioxane along with 1.0 g of activated 3 A molecular sieves. The reaction was heated in an oil bath at 100° C. for 1 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)-4,4-dimethylpyrrolidin-2-one. Mass Spectrum (ESI) m/e=325.1 (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-8d5d06b6d71b4bf09eef9bc2ea80e631
Source dataset: uspto-grants-2015_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08940724B2

Reaction notes

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