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

HRID 1431437ノート

反応式

HRID 1431437 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[CH2:20][CH2:19][CH2:18][C:17]1=[O:21].CN[C@H]1CCCC[C@@H]1NC.[O-]P([O-])([O-])=O.[K+].[K+].[K+]>O1CCOCC1.[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[CH2:20][CH2:19][CH2:18][C:17]2=[O:21])[C:11]=1[CH3:12]

参加物

7

反応物 4

HCID 120252-PyrrolidoneHCID 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 596310731-(4-Bromo-5,7-difluoro-3-methylquinolin-2-yl)pyrrolidin-2-one

試薬・触媒・溶媒 2

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

反応条件

温度
110 °C

実験手順

The 2,4-dibromo-5,7-difluoro-3-methylquinoline (500 mg, 1.50 mmol), pyrrolidin-2-one (0.110 mL, 1.50 mmol), copper (I) iodide (14 mg, 0.074 mmol), (1S,2S)—N1,N2-dimethylcyclohexane-1,2-diamine (0.023 mL, 0.150 mmol) and potassium phosphate tribasic (630 mg, 3.00 mmol) were slurried in dioxane (5 mL) and stirred in a microwave reactor at 110° C. for 2 h. The resulting slurry was dissolved and partitioned between water and EtOAc (2×75 mL). The combined organic layers were washed with brine (1×50 mL) and dried over magnesium sulfate. The crude product was purified by medium pressure chromatography (silica, 0 to 100% EtOAc:DCM) to give 1-(4-bromo-5,7-difluoro-3-methylquinolin-2-yl)pyrrolidin-2-one. Mass Spectrum (ESI) m/e=341.0 (M+1).

後処理

  1. dissolutionThe resulting slurry was dissolved
  2. custompartitioned between water and EtOAc (2×75 mL)
  3. washThe combined organic layers were washed with brine (1×50 mL)
  4. dry with materialdried over magnesium sulfate
  5. customThe crude product was purified by medium pressure chromatography (silica, 0 to 100% EtOAc:DCM)

出典と根拠

ORDレコード
ord-3920e3decf2842c28c1a5c1794b92733
出典データセット
uspto-grants-2015_01
特許番号
US08940724B2

反応ノート

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