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

Temperature

100 °C

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

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)

ORD record

ord-0635097244414d89aa1bc38df1a955a2

Source dataset

uspto-grants-2013_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08362065B2