Toluene → 5-Chloro-1-methyl-1H-indol-2-ylmethyl methylamine

To a solution of 5-chloro-1-methyl-1H-indole-2-carboxylic acid ethyl ester (1.27 g, 5.3 mmol) in toluene (10 mL) was added ON-dimethyl-hydroxylamine (9.6 mL of a 1 M solution in toluene, 9.6 mmol). The resulting mixture was heated to reflux overnight after which the reaction was cooled to room temperature and quenched by the addition of 10% aqueous K2CO3 (50 mL). The mixture was extracted with ethyl acetate (3×200 mL). The combined organic layers were washed with brine (100 mL), dried over Na2SO4, filtered and concentrated to give the title compound (2.12 g, 96%) as a yellow solid: 1H NMR (300 MHz, CDCl3) δ 7.59 (s, 1H), 7.27 (m, 2H), 6.73 (s, 1H), 6.13 (s, 1H), 4.03 (s, 3H), 3.01 (d, J=4.9 Hz, 3H); MS (ESI) m/e 222 (M+H)+.

1. temperatureThe resulting mixture was heated
2. temperatureto reflux overnight after which the reaction
3. customquenched by the addition of 10% aqueous K2CO3 (50 mL)
4. extractionThe mixture was extracted with ethyl acetate (3×200 mL)
5. washThe combined organic layers were washed with brine (100 mL)
6. dry with materialdried over Na2SO4
7. filtrationfiltered
8. concentrationconcentrated

ORD-Eintrag

ord-e07d61f6bd8a4822a654135b5d8d9391

Quelldatensatz

uspto-grants-2010_09

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US07790709B2