Water → 1H-Pyrrolo[3,2-b]pyridine, 3-ethyl-5-(trifluoromethyl)-

Temperatur

100 °C

A solution of N-but-2-enyl-2,2,2-trifluoro-N-(2-iodo-6-trifluoromethyl-pyridin-3-yl)-acetamide (5.2 g, 11.9 mmol) in DMF (24 mL) is treated with n-Bu4NCl (3.6 g, 13.1 mmol), Pd(OAc)2 (107 mg, 0.48 mmol), and stirred at 100° C. for 1 h. H2O (10 mL) is added, and the mixture is cooled to rt and filtered through a pad of silica gel. The filtrate is extracted with EtOAc/heptane (3×50 mL) (1:1). The combined organic layer is dried (Na2SO4), filtered and concentrated in vacuo. The residue is purified by silica gel chromatography eluting with 5%-50% EtOAc in heptane to afford 3-ethyl-5-trifluoromethyl-1H-pyrrolo[3,2-b]pyridine (2.2 g, 86%). MS: 215 (M+H); 1H NMR (300 MHz, CDCl3): δ 8.24 (s, NH, 1H), 7.73 (d, 1H), 7.50 (d, 1H), 7.34 (d, 1H), 2.93 (q, 2H), 1.36 (t, 3H).

1. temperaturethe mixture is cooled to rt
2. filtrationfiltered through a pad of silica gel
3. extractionThe filtrate is extracted with EtOAc/heptane (3×50 mL) (1:1)
4. dry with materialThe combined organic layer is dried (Na2SO4)
5. filtrationfiltered
6. concentrationconcentrated in vacuo
7. customThe residue is purified by silica gel chromatography
8. washeluting with 5%-50% EtOAc in heptane

ORD-Eintrag

ord-0a9dd70a4799485d8ca5c0e9b0769449

Quelldatensatz

uspto-grants-2012_09

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US08258130B2