N,N'-Dimethylethylenediamine → HCID 66772514, compound

Temperature

110 °C

To a solution of methyl 1H-indole-4-carboxylate (3.0 g, 17.1 mmol) in DMSO (25 mL) and 1,4-dioxane (25 mL) in a sealed tube were added potassium phosphate (7.3 g, 34.3 mmol), dimethylethylenediamine (1.0 mL, 9.1 mmol), L-proline (1.1 g, 9.1 mmol), 1-bromo-4-fluorobenzene (1.3 mL, 11.42 mmol), and copper iodide (1.1 g, 5.7 mmol). The mixture was purged with argon gas; the tube was sealed and heated at 110° C. overnight. The reaction mixture was cooled down to rt, washed with water (100 mL) and the aqueous mixture was extracted with dichloromethane (3×150 mL). The combined organic layers were dried (Na2SO4), filtered, and concentrated under reduced pressure. Purification of the resulting residue by column chromatography (0% to 50% dichloromethane in hexanes) afforded methyl 1-(4-fluorophenyl)-1H-indole-4-carboxylate (2.1 g, 68%) as a white solid: 1H NMR (300 MHz, DMSO) δ 7.87-7.82 (m, 2H), 7.75 (d, J=8.4 Hz, 1H), 7.68-7.63 (m, 2H), 7.49-7.42 (m, 2H), 7.32 (t, J=7.8 Hz, 1H), 7.20 (dd, J=3.0, 0.9 Hz, 1H), 3.93 (s, 3H); MS (ESI+) m/z 270 [M+H]+.

1. customThe mixture was purged with argon gas
2. customthe tube was sealed
3. temperatureThe reaction mixture was cooled down to rt
4. washwashed with water (100 mL)
5. extractionthe aqueous mixture was extracted with dichloromethane (3×150 mL)
6. dry with materialThe combined organic layers were dried (Na2SO4)
7. filtrationfiltered
8. concentrationconcentrated under reduced pressure
9. customPurification of the resulting residue by column chromatography (0% to 50% dichloromethane in hexanes)

ORD record

ord-60e5d2efd45845e8ba7553ff50a9a76c

Source dataset

uspto-grants-2014_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08710047B2