Cesium carbonate → 1-(4-Chloro-7-fluoro-3-methylquinolin-2-yl)-4,4-dimethylpyrrolidin-2-one

HRID 1431778Notes

Reaction equation

HRID 1431778 reaction equation
Cl[C:2]1[C:11]([CH3:12])=[C:10]([Cl:13])[C:9]2[C:4](=[CH:5][C:6]([F:14])=[CH:7][CH:8]=2)[N:3]=1.[CH3:15][C:16]1([CH3:22])[CH2:20][NH:19][C:18](=[O:21])[CH2:17]1.C(=O)([O-])[O-].[Cs+].[Cs+].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>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].O1CCOCC1>[Cl:13][C:10]1[C:9]2[C:4](=[CH:5][C:6]([F:14])=[CH:7][CH:8]=2)[N:3]=[C:2]([N:19]2[CH2:20][C:16]([CH3:22])([CH3:15])[CH2:17][C:18]2=[O:21])[C:11]=1[CH3:12]

Participants

7

Reactant 4

HCID 10796Cesium carbonateHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 6375934,4-Dimethyl-2-pyrrolidinoneHCID 596311082,4-Dichloro-7-fluoro-3-methylquinoline

Product 1

HCID 596313401-(4-Chloro-7-fluoro-3-methylquinolin-2-yl)-4,4-dimethylpyrrolidin-2-one

Reagents, catalysts & solvents 2

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 312751,4-DioxaneSolvent

Procedure

Prepared according to Procedure F using 2,4-dichloro-7-fluoro-3-methylquinoline (0.300 g, 1.304 mmol), 4,4-dimethyl-2-pyrrolidinone (0.162 mL, 1.434 mmol), cesium carbonate (0.600 g, 1.826 mmol), tris(dibenzylideneacetone)dipalladium (0) (0.060 g, 0.065 mmol), XantPhos (0.113 g, 0.196 mmol), and dioxane (2.6 mL). Purification by column chromatography (silica; 0-20% EtOAc in hexanes) afforded 1-(4-chloro-7-fluoro-3-methylquinolin-2-yl)-4,4-dimethylpyrrolidin-2-one as a white amorphous solid. Mass Spectrum (ESI) m/e=307.0 (M+1).

Workup

  1. customPrepared
  2. customPurification by column chromatography (silica; 0-20% EtOAc in hexanes)

Sources & evidence

ORD record
ord-31775dea529341c0a1187062f74520f7
Source dataset
uspto-grants-2015_01
Patent number
US08940724B2

Reaction notes

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