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

HRID 661828노트

반응식

HRID 661828 반응식
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

참가 물질

7

반응물 4

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

생성물 1

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

시약·촉매·용매 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)촉매HCID 312751,4-Dioxane용매

반응 조건

온도
100 °C

실험 절차

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 (1H, s), 8.42 (1H, s), 7.84 (1H, d, J=7.77 Hz), 7.37 (1H, d, J=7.77 Hz), 7.34 (1H, s), 4.73 (2H, s), 2.50 (3H, s), 2.35 (3H, s). Mass spectrum m/z 317, 319 (M+H)+.

후처리

  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)

출처 및 근거

ORD 기록
ord-a2c4ad030fb54265af157e0a01be2f39
출처 데이터셋
uspto-grants-2011_12
특허 번호
US08084620B2

반응 노트

불러오는 중…