N,N'-Dimethylethylenediamine → HCID 59375096、化合物

HRID 1811011ノート

反応式

HRID 1811011 の反応式
[F:1][C:2]1[C:3](I)=[N:4][CH:5]=[CH:6][C:7]=1[I:8].[C:10]1(=[O:19])[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH2:12][NH:11]1.C(=O)([O-])[O-].[K+].[K+].CNCCNC>O1CCOCC1.[Cu]I>[F:1][C:2]1[C:3]([N:11]2[CH2:12][C:13]3[C:18](=[CH:17][CH:16]=[CH:15][CH:14]=3)[C:10]2=[O:19])=[N:4][CH:5]=[CH:6][C:7]=1[I:8]

参加物

7

反応物 4

HCID 8070N,N'-DimethylethylenediamineHCID 10199PhthalimidineHCID 11430Potassium CarbonateHCID 99979273-Fluoro-2,4-diiodopyridine

生成物 1

HCID 59375096HCID 59375096、化合物収率 41%

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

A mixture of 3-fluoro-2,4-diiodopyridine (300 mg, 0.860 mmol), isoindolin-1-one (114 mg, 0.860 mmol), copper (I) iodide (8.19 mg, 0.043 mmol), potassium carbonate (238 mg, 1.720 mmol) and N1,N2-dimethylethane-1,2-diamine (7.58 mg, 0.086 mmol) in 1,4-dioxane (5 mL) was heated at 110° C. in a sealed tube for 15 h. The mixture was cooled to rt, filtered through Celite and washed with DCM. The filtrate was concentrated and the residue was purified by column chromatography (eluting with a gradient from 80:20 hexane-EtOAc to EtOAc) to give 2-(3-fluoro-4-iodopyridin-2-yl)isoindolin-1-one (125 mg, 41%). 1H NMR (400 MHz, chloroform-d) δ 7.86-8.06 (2 H, m), 7.41-7.71 (4 H, m), 5.04 (2 H, s). Mass spectrum m/z 354.9 (M+H)+.

後処理

  1. temperatureThe mixture was cooled to rt
  2. filtrationfiltered through Celite
  3. washwashed with DCM
  4. concentrationThe filtrate was concentrated
  5. customthe residue was purified by column chromatography (
  6. washeluting with a gradient from 80:20 hexane-EtOAc to EtOAc)

出典と根拠

ORDレコード
ord-acf015592d0143889f12118095992fe2
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…