HCID 131734533, compound → HCID 63097602, compound

Temperature

60 °C

The mixture of 6-((2,4-dichlorobenzyl)oxy)-N-methoxy-1-benzofuran-3(2H)-imine (1.23 g) and THF (dry) (36 mL) was added dropwise to a solution of borane tetrahydrofuran complex solution (1.0 mol/L, 7.27 mL) at 0° C. The mixture was stirred at 60° C. overnight. After cooling, the mixture was quenched with water and 1N NaOH (15 mL). The mixture was stirred at 60° C. for 5 h. After cooling, the mixture was extracted with EtOAc. The combined organic layer was washed with brine, dried over MgSO4, and concentrated in vacuo. The solid was dissolved in EtOAc and to the solution was added 4M HCl in EtOAc dropwise. The precipitate (850 mg) was collected by filtration. The solid was dissolved in 28% aqueous ammonia and extracted with EtOAc. The combined organic layer was washed with brine, dried over MgSO4, and concentrated in vacuo to give the title compound (721.3 mg).

1. temperatureAfter cooling
2. customthe mixture was quenched with water and 1N NaOH (15 mL)
3. stirringThe mixture was stirred at 60° C. for 5 h
4. temperatureAfter cooling
5. extractionthe mixture was extracted with EtOAc
6. washThe combined organic layer was washed with brine
7. dry with materialdried over MgSO4
8. concentrationconcentrated in vacuo
9. dissolutionThe solid was dissolved in EtOAc and to the solution
10. additionwas added 4M HCl in EtOAc dropwise
11. filtrationThe precipitate (850 mg) was collected by filtration
12. dissolutionThe solid was dissolved in 28% aqueous ammonia
13. extractionextracted with EtOAc
14. washThe combined organic layer was washed with brine
15. dry with materialdried over MgSO4
16. concentrationconcentrated in vacuo

ORD record

ord-91d598594a7d427aa39ab77b01a4afe1

Source dataset

uspto-grants-2016_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09238639B2