Isopropyl iodide → HCID 70089281, compound

To a solution of N-(tropan-4-yl)-1H-indazole-3-carboxamide (2.98 g, 10 mmol) in 75 mL of dimethylformamide under a nitrogen atmosphere was added, in portions, sodium hydride (60% dispersion in mineral oil, 420 mg, 10 mmol). The resulting solution was allowed to stir for about 1 hour at room temperature before adding 2-iodopropane (1.2 mL, 12 mmol). This resulting solution was allowed to stir at room temperature for about 18 hours. The dimethylformamide was evaporated under reduced pressure and the residue was dissolved in about 100 mL of 1N hydrochloric acid. The acidic solution was washed with ethyl acetate and then cooled before making it basic with saturated aqueous sodium carbonate. The basic mixture was extracted 3 times with methylene chloride. The extracts were washed with brine, dried over sodium sulfate, filtered, then evaporated under reduced pressure to give a viscous oil. The oil was purified by preparative HPLC (gradient methylene chloride:methanol 0-25%, 1% ammonium hydroxide) to give 2.52 g of an oil. Yield: 77%. MS(FD) M+326.

1. stirringto stir at room temperature for about 18 hours
2. customThe dimethylformamide was evaporated under reduced pressure
3. dissolutionthe residue was dissolved in about 100 mL of 1N hydrochloric acid
4. washThe acidic solution was washed with ethyl acetate
5. temperaturecooled
6. extractionThe basic mixture was extracted 3 times with methylene chloride
7. washThe extracts were washed with brine
8. dry with materialdried over sodium sulfate
9. filtrationfiltered
10. customevaporated under reduced pressure
11. customto give a viscous oil
12. customThe oil was purified by preparative HPLC (gradient methylene chloride:methanol 0-25%, 1% ammonium hydroxide)

ORD record

ord-a63acd3cdb9c41b3b1d48ce5b215b6b9

Source dataset

uspto-grants-2000_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06069152