Potassium Carbonate → HCID 22138907, compound

To a stirred suspension of 6-nitroindazole (10 g, 61 mmol) and K2CO3 (9.31 g, 67.5 mmol) in N,N-dimethylformamide (60 mL) at room temperature was added bromoacetaldehyde dimethylacetal (8.0 mL, 67.5 mmol) and the reaction was heated to 55 C for 18 ours. The mixture was allowed to cool and was diluted with diethyl ether (30 mL) and H2O (60 mL). The layers were separated and the aqueous was extracted with additional diethyl ether (3×30 mL). The combined organic layers were dried with anhydrous Na2SO4, filtered and concentrated under reduced pressure to an orange oil. The residue was purified by MPLC (SiO2, 9:1 Hx:Ethyl acetateto 4:1 Hx:EtoAc) to yield the titled product as a yellow solid. 1H NMR (300 MHz, DMSO-d6) δ ppm 3.31 (m, 6 H), 4.67 (d, J=5.42 Hz, 2 H), 4.91 (t, J=5.42 Hz, 1H), 7.82 (m1 H), 7.99 (m, 1 H) and 8.63 (s, 2 H); MS (ESI) 252 (M+H)+.

1. temperaturethe reaction was heated to 55 C for 18 ours
2. temperatureto cool
3. customThe layers were separated
4. extractionthe aqueous was extracted with additional diethyl ether (3×30 mL)
5. dry with materialThe combined organic layers were dried with anhydrous Na2SO4
6. filtrationfiltered
7. concentrationconcentrated under reduced pressure to an orange oil
8. customThe residue was purified by MPLC (SiO2, 9:1 Hx:Ethyl acetateto 4:1 Hx:EtoAc)

ORD record

ord-e87c675f936448b8a0f38e01c3e767dd

Source dataset

uspto-grants-2006_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07049307B2