Sodium Iodide → 6-(4-(4-(2,3-dichlorophenyl)-1,4-diazepan-1-yl)butoxy)-1H-indazole

A mixture of intermediate 51 (54.2 mg, 0.20 mmol) and NaI (60.3 mg, 0.40 mmol) in CH3CN (3 mL) was heated to reflux for 30 min and then cooled to rt. To this mixture was added intermediate 2 (62.4 mg, 0.22 mmol), followed then by DIEA (0.077 mL, 0.44 mmol). The resulting mixture was heated to reflux and stirred for 4 h. Precipitated crystals were filtered off and the filtrate was evaporated under reduced pressure. The residue was extracted with EtOAc. The combined EtOAc layers were washed with brine, dried over anhydrous Na2SO4, concentrated in vacuo and purified by ISCO to give 6-(4-(4-(2,3-dichlorophenyl)-1,4-diazepan-1-yl)butoxy)-1H-indazole (compound 47) (50.8 mg, 59%). HPLC: 99%, RT 4.526 min. MS (ESI) m/z 433.20 [M+H]+.

1. temperaturewas heated
2. temperatureto reflux for 30 min
3. temperatureThe resulting mixture was heated
4. temperatureto reflux
5. customPrecipitated crystals
6. filtrationwere filtered off
7. customthe filtrate was evaporated under reduced pressure
8. extractionThe residue was extracted with EtOAc
9. washThe combined EtOAc layers were washed with brine
10. dry with materialdried over anhydrous Na2SO4
11. concentrationconcentrated in vacuo
12. custompurified by ISCO

ORD record

ord-0a33ef7f1c7d467f98a0de611fc1566e

Source dataset

uspto-grants-2015_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09156822B2