N,N'-Dimethylethylenediamine → 2-(5-Bromo-4-methylpyridin-3-yl)-5-methylisoindolin-1-one

HRID 1811010ノート

反応式

HRID 1811010 の反応式
Br[C:2]1[CH:3]=[N:4][CH:5]=[C:6]([Br:9])[C:7]=1[CH3:8].C[C:11]1[CH:19]=[C:18]2[C:14]([CH2:15][NH:16][C:17]2=[O:20])=[CH:13][CH:12]=1.[C:21](=O)([O-])[O-].[K+].[K+].CNCCNC>O1CCOCC1.[Cu]I>[Br:9][C:6]1[C:7]([CH3:8])=[C:2]([N:16]2[CH2:15][C:14]3[C:18](=[CH:19][CH:11]=[C:12]([CH3:21])[CH:13]=3)[C:17]2=[O:20])[CH:3]=[N:4][CH:5]=1

参加物

7

反応物 4

HCID 8070N,N'-DimethylethylenediamineHCID 11430Potassium CarbonateHCID 8193383,5-Dibromo-4-methylpyridineHCID 124964736-Methyl-2,3-dihydro-1H-isoindol-1-one

生成物 1

HCID 593751432-(5-Bromo-4-methylpyridin-3-yl)-5-methylisoindolin-1-one収率 30.1%

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
100 °C

実験手順

Step 2 A mixture of 3,5-dibromo-4-methylpyridine (2.00 g, 7.97 mmol), 6-methylisoindolin-1-one (1.173 g, 7.97 mmol), copper (I) iodide (0.076 g, 0.399 mmol), potassium carbonate (2.203 g, 15.94 mmol) and N1,N2-dimethylethane-1,2-diamine (0.070 g, 0.797 mmol) in 1,4-dioxane (20 mL) was heated at 100° C. for 15 h. The mixture was cooled to rt, filtered through Celite and washed with DCM. The filtrate was diluted with DCM (100 mL) and washed with water (10 mL) and brine (10 mL), then was dried and concentrated. The residue was purified by column chromatography (eluting with a gradient from 80:20 hexane-EtOAc to EtOAc) to give 2-(5-bromo-4-methylpyridin-3-yl)-5-methylisoindolin-1-one (760 mg, 30%). 1H NMR (400 MHz, chloroform-d) δ 8.68 (1 H, s), 8.42 (1 H, s), 7.84 (1 H, d, J=7.77 Hz), 7.37 (1 H, d, J=7.77 Hz), 7.34 (1 H, s), 4.73 (2 H, s), 2.50 (3 H, s), 2.35 (3 H, s). Mass spectrum m/z 317, 319 (M+H)+.

後処理

  1. temperatureThe mixture was cooled to rt
  2. filtrationfiltered through Celite
  3. washwashed with DCM
  4. additionThe filtrate was diluted with DCM (100 mL)
  5. washwashed with water (10 mL) and brine (10 mL)
  6. customwas dried
  7. concentrationconcentrated
  8. customThe residue was purified by column chromatography (
  9. washeluting with a gradient from 80:20 hexane-EtOAc to EtOAc)

出典と根拠

ORDレコード
ord-0635097244414d89aa1bc38df1a955a2
出典データセット
uspto-grants-2013_01
特許番号
US08362065B2

反応ノート

読み込み中…