Diisopropylethylamine → 6-((4-chlorophenyl)(hydroxy)(1-methyl-1H-imidazol-5-yl)methyl)-1-methyl-4-(3-((trimethylsilyl)ethynyl)phenyl)-1,8-naphthyridin-2(1H)-one

To a solution of 5-bromo-1-methylimidazole (0.68 g, 4.26 mmol) in dry DCM (15 mL), DIPEA (0.77 mL, 4.47 mmol) and iPrMgCl (2.13 mL, 4.26 mmol, 2.0 M solution in THF) was added at 10° C. The reaction mixture was stirred for 1.5 h and a solution of compound J (0.5 g, 1.06 mmol) in DCM was added to it. The reaction mixture was refluxed for 2 h and quenched with saturated NH4Cl solution. The product was extracted with DCM (30 mL). The organic layer was dried, filtered and concentrated to give crude c. Purification of the crude product provided 210 mg (36%) of compound K.

1. temperatureThe reaction mixture was refluxed for 2 h
2. customquenched with saturated NH4Cl solution
3. extractionThe product was extracted with DCM (30 mL)
4. customThe organic layer was dried
5. filtrationfiltered
6. concentrationconcentrated
7. customto give crude c
8. customPurification of the crude product

ORD record

ord-e6a68075a5ae407c8c14952fed5ff5dd

Source dataset

uspto-grants-2013_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08343996B2