Methoxymethyl-triphenylphosphonium chloride → HCID 89690325, compound

To a stirred solution of (methoxymethyl)triphenylphosphonium chloride (4.98 g) in THF (20 ml) was added lithium hexamethyldisilazide (1.0 M solution in hexane, 29 ml) at −15° C., and the resulting mixture was stirred at the same temperature for 30 min. A solution of 3-(6-bromo-1-methyl-1H-benzimidazol-2-yl)cyclobutanone (2.7 g) in THF (5 ml) was added to the reaction mixture, and the resulting mixture was stirred at room temperature for 16 h. The reaction mixture was quenched with saturated NH4Cl solution, concentrated in vacuo and diluted with EtOAc. The organic layer was washed with brine, dried over Na2SO4, concentrated in vacuo and purified by column chromatography (hexane/EtOAc) to afford the title compound (850 mg) as a yellow solid.

1. stirringthe resulting mixture was stirred at room temperature for 16 h
2. customThe reaction mixture was quenched with saturated NH4Cl solution
3. concentrationconcentrated in vacuo
4. additiondiluted with EtOAc
5. washThe organic layer was washed with brine
6. dry with materialdried over Na2SO4
7. concentrationconcentrated in vacuo
8. custompurified by column chromatography (hexane/EtOAc)

ORD record

ord-f7eb5597bd3a4a0db8fa3f43eca9bb44

Source dataset

uspto-grants-2016_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09365540B2