Iodine → (2,3-Dihydro-benzo[1,4]dioxin-6-yl)-(4-iodo-pyridin-2-yl)-amine

HRID 730301

反応式

HRID 730301 の反応式
[O:1]1[C:6]2[CH:7]=[CH:8][C:9]([NH:11][C:12]3[CH:17]=[C:16](N)[CH:15]=[CH:14][N:13]=3)=[CH:10][C:5]=2[O:4][CH2:3][CH2:2]1.[I-:19].[K+].II>COCCOC.[Cu]I>[O:1]1[C:6]2[CH:7]=[CH:8][C:9]([NH:11][C:12]3[CH:17]=[C:16]([I:19])[CH:15]=[CH:14][N:13]=3)=[CH:10][C:5]=2[O:4][CH2:3][CH2:2]1

参加物

6

反応物 3

HCID 807IodineHCID 4875Potassium IodideHCID 57808069N2-(2,3-Dihydro-benzo[1,4]dioxin-6-yl)-pyridine-2,4-diamine

生成物 1

HCID 57808271(2,3-Dihydro-benzo[1,4]dioxin-6-yl)-(4-iodo-pyridin-2-yl)-amine

試薬・触媒・溶媒 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)触媒HCID 80711,2-Dimethoxyethane溶媒

反応条件

温度
62.5 °C

実験手順

Isopentyl nitrile (Aldrich Chemical Company) (3.9 mL, 29 mmol) was added to a mixture of N2-(2,3-dihydro-benzo[1,4]dioxin-6-yl)-pyridine-2,4-diamine (Example 2(a), 2.4 g, 9.8 mmol), potassium iodide (Aldrich Chemical Company) (1.6 g, 9.8 mmol), iodine (Aldrich Chemical Company) (1.2 g, 4.9 mmol) and copper (I) iodide (Aldrich Chemical Company) (1.9 g, 9.8 mmol) in 1,2-dimethoxyethane (60 mL). The reaction mixture was heated at 60-65° C. for 1 hr. After cooling to room temperature, the insoluble materials were removed by filtration and the filtrate was diluted with EtOAc, washed with 25% aqueous NH4OH, 5% aqueous sodium bisulfite and then brine. The organic layer was separated, dried over Na2SO4 and concentrated in vacuo. The residue was purified on a Biotage 40 M column (2.5:1 hexane:EtOAc) to give the title compound as an off-white solid. MS (ESI, pos. ion) m/z: 355 (M+1).

後処理

  1. temperatureAfter cooling to room temperature
  2. customthe insoluble materials were removed by filtration
  3. additionthe filtrate was diluted with EtOAc
  4. washwashed with 25% aqueous NH4OH, 5% aqueous sodium bisulfite
  5. customThe organic layer was separated
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated in vacuo
  8. customThe residue was purified on a Biotage 40 M column (2.5:1 hexane:EtOAc)

出典と根拠

ORDレコード
ord-c79233cb225e4a3db5c6eaf432d4190d
出典データセット
uspto-grants-2009_09
特許番号
US07582657B2

関連ノート

読み込み中…