2-Piperidone → 1-(4-Bromo-5,7-difluoro-3-methylquinolin-2-yl)piperidin-2-one

HRID 1431606ノート

反応式

HRID 1431606 の反応式
Br[C:2]1[C:11]([CH3:12])=[C:10]([Br:13])[C:9]2[C:4](=[CH:5][C:6]([F:15])=[CH:7][C:8]=2[F:14])[N:3]=1.[NH:16]1[CH2:21][CH2:20][CH2:19][CH2:18][C:17]1=[O:22].CN[C@H]1CCCC[C@@H]1NC.[O-]P([O-])([O-])=O.[K+].[K+].[K+]>O1CCOCC1.O.[Cu]I>[Br: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:16]2[CH2:21][CH2:20][CH2:19][CH2:18][C:17]2=[O:22])[C:11]=1[CH3:12]

参加物

8

反応物 4

HCID 126652-PiperidoneHCID 62657Potassium Phosphate, TribasicHCID 13822957(1S,2S)-(+)-N,N'-Dimethylcyclohexane-1,2-diamineHCID 596311142,4-Dibromo-5,7-difluoro-3-methylquinoline

生成物 1

HCID 596310611-(4-Bromo-5,7-difluoro-3-methylquinolin-2-yl)piperidin-2-one

試薬・触媒・溶媒 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)触媒HCID 962Water溶媒HCID 312751,4-Dioxane溶媒

実験手順

The 2,4-dibromo-5,7-difluoro-3-methylquinoline (2.00 g, 5.90 mmol), piperidin-2-one (590 mg, 5.90 mmol), copper (I) iodide (57.0 mg, 0.300 mmol), (1S,2S)—N1,N2-dimethylcyclohexane-1,2-diamine (0.094 mL, 0.59 mmol) and potassium phosphate tribasic (2.50 g, 12.0 mmol) were combined in 1,4-dioxane (10 mL) and stirred in the microwave reactor for 3.5 h. The reaction was diluted with water and extracted with EtOAc (2×100 mL). The combined organic layers were washed with brine and dried over magnesium sulfate. The crude product was then purified by medium pressure chromatography (silica gel, 0 to 100% EtOAc: hexanes) to give 1-(4-bromo-5,7-difluoro-3-methylquinolin-2-yl)piperidin-2-one. Mass Spectrum (ESI) m/e=355.1 (M+1).

後処理

  1. extractionextracted with EtOAc (2×100 mL)
  2. washThe combined organic layers were washed with brine
  3. dry with materialdried over magnesium sulfate
  4. customThe crude product was then purified by medium pressure chromatography (silica gel, 0 to 100% EtOAc: hexanes)

出典と根拠

ORDレコード
ord-b3401476a4c84d07816b1d1019276c9b
出典データセット
uspto-grants-2015_01
特許番号
US08940724B2

反応ノート

読み込み中…