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

HRID 1431778노트

반응식

HRID 1431778 반응식
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]

참가 물질

7

반응물 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

생성물 1

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

시약·촉매·용매 2

HCID 9811564Bis(dibenzylideneacetone)palladium촉매HCID 312751,4-Dioxane용매

실험 절차

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).

후처리

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

출처 및 근거

ORD 기록
ord-31775dea529341c0a1187062f74520f7
출처 데이터셋
uspto-grants-2015_01
특허 번호
US08940724B2

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