Methyl iodide → 5H-Pyrrolo(3,4-b)pyridine-5,7(6H)-dione, 6-methyl-

HRID 965617ノート

反応式

HRID 965617 の反応式
[CH:1]1[C:6]2[C:7]([NH:9][C:10](=[O:11])[C:5]=2[CH:4]=[N:3][CH:2]=1)=[O:8].[H-].[Na+].CI.[C:16](OCC)(=O)C>CN(C)C=O>[CH3:16][N:9]1[C:7](=[O:8])[C:6]2[CH:1]=[CH:2][N:3]=[CH:4][C:5]=2[C:10]1=[O:11]

参加物

6

反応物 4

HCID 6328Methyl iodideHCID 8857Ethyl AcetateHCID 24758Sodium hydrideHCID 729263,4-Pyridinedicarboximide

生成物 1

HCID 1388335H-Pyrrolo(3,4-b)pyridine-5,7(6H)-dione, 6-methyl-

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

To a stirred solution of 3,4-pyridinedicarboximide (10.0 g, 67.5 mmol) in N,N-dimethylformamide was added sodium hydride (1.55 g, 60% dispersion in mineral oil, 67.5 mmol) at room temperature. The mixture was stirred for about 30 minutes, then methyl iodide (9.58 g 67.5 mmol) was added, and the reaction was stirred overnight. Ethyl acetate was added to the reaction mixture, and the mixture was extracted once with water, twice with brine. The organic layer was dried over anhydrous magnesium sulfate, filtered and concentrated in vacuo (azeotroping excess N,N-dimethylformamide with heptanes) to give crude product. Purification by silica gel chromatography using 0-5% methanol/dichloromethane as eluent afforded the title compound of part 11-A as an off-white solid (5 g, 46%): PB MS (M+1)+ 163; 1H NMR=250 MHz (CDCl3) δ: 9.11 (arom, s, 1H), 9.08 (arom, d, 1H), 7.75 (arom, d, 1 H), 3.20 (Me, s, 3H).

後処理

  1. stirringthe reaction was stirred overnight
  2. extractionthe mixture was extracted once with water, twice with brine
  3. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo (azeotroping excess N,N-dimethylformamide with heptanes)
  6. customto give crude product
  7. customPurification by silica gel chromatography

出典と根拠

ORDレコード
ord-b77b4fe8db3e491e8257d8f26068ceef
出典データセット
uspto-grants-2005_10
特許番号
US06951850B2

反応ノート

読み込み中…