Indole → HCID 21809418, compound

Temperature

0 °C

NaH (0.444 g, 11.1 mmol) was dissolved in anhydrous DMF (5 mL) under argon and cooled to 0° C. To it was added 1H-indole (1.00 g, 8.54 mmol) dissolved in anhydrous DMF (5 mL). The reaction was stirred for 15 min at 0° C. followed by the addition of ethyl 3-bromopropanoate (1.10 mL, 8.54 mmol). The reaction was then stirred for 3 h at 70° C. and then quenched by the addition of H2O (30 mL). The organic products were extracted with EtOAc (3×30 mL), washed with H2O (2×30 mL), brine (15 mL), dried with Na2SO4, filtered and concentrated in vacuo. The crude product was purified using automated column chromatography method 1 to yield ethyl 3-(1H-indol-1-yl)propanoate (0.759 g, 3.49 mmol). The title compound was then prepared from ethyl 3-(1H-indol-1-yl)propanoate (0.486 g, 5.52 mmol) according to General Procedure B (prep. HPLC method 1) and isolated as a white solid (0.104 g, 23%). 1H NMR (400 MHz, MeOD): δ 7.53 (d, J=7.83 Hz, 1H), 7.42 (d, J=8.1 Hz, 1H), 7.16 (m, 2H), 7.02 (t, J=7.4 Hz, 1H), 6.41 (d, J=2.8 Hz, 1H), 4.48 (t, J=6.5 Hz, 2H), 2.56 (t, J=6.6 Hz, 2H). ESI-LRMS: [M+H]+=205.1 m/z. ESI-HRMS: calc. for C11H12N2O2: [M+H]+=205.0972 m/z, found: [M+H]+=205.0971 m/z.

1. stirringThe reaction was then stirred for 3 h at 70° C.
2. customquenched by the addition of H2O (30 mL)
3. extractionThe organic products were extracted with EtOAc (3×30 mL)
4. washwashed with H2O (2×30 mL), brine (15 mL)
5. dry with materialdried with Na2SO4
6. filtrationfiltered
7. concentrationconcentrated in vacuo
8. customThe crude product was purified

ORD record

ord-e6653dc912aa49069b614cb5cefff9bc

Source dataset

uspto-grants-2016_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09249087B2