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

HRID 1060570노트

반응식

HRID 1060570 반응식
[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]

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

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, 1H), 3.20 (Me, s, 3H).

후처리

  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

출처 및 근거

ORD 기록
ord-e28de7c106474ac79e9a40064fc1be62
출처 데이터셋
uspto-grants-2003_02
특허 번호
US06525047B2

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