Sodium hydride → tert-butyl 6-bromo-5-chloropyridin-2-yl((4-methoxytetrahydro-2H-pyran-4-yl)methyl)carbamate

To a stirred solution of tert-butyl 6-bromo-5-chloropyridin-2-ylcarbamate (140 mg, 0.455 mmol) in DMF (2 ml) under nitrogen was added NaH (60%, 30 mg, 0.774 mmol). The resulting mixture was stirred at ambient temperature for one hour. A solution of (4-methoxytetrahydro-2H-pyran-4-yl)methyl 4-methylbenzenesulfonate (intermediate O, 164 mg, 0.546 mmol) in DMF (1.5 ml) was then added to the preceding mixture. The resulting mixture was then stirred overnight at about 85° C. The stirred mixture was diluted with 30 ml of ethyl acetate, washed with water (20 ml×3) and dried. After concentration the resulting residue was purified by silica gel chromatography using a 12 g column, eluting with 5-20% ethyl acetate in hexane to yield the desired compound “P” as a viscous oil (92 mg), which solidified upon standing overnight. LCMS (m/z): 437.0 [M+H]+; Retention time=1.158 min.

1. stirringThe resulting mixture was then stirred overnight at about 85° C
2. washwashed with water (20 ml×3)
3. customdried
4. concentrationAfter concentration the resulting residue
5. customwas purified by silica gel chromatography
6. washeluting with 5-20% ethyl acetate in hexane

ORDレコード

ord-0834749bb03f4136b17743394a1f7a26

出典データセット

uspto-grants-2013_04

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US08415381B2