Potassium Carbonate → (E)-3-[3'-adamantan-1-yl-4'-(2-morpholin-4-yl-ethoxy)biphenyl-4-yl]-acrylic acid methyl ester

K2CO3 (265 mg, 1.92 mmol) was added to a solution of (E)-3-(3′-adamantan-1-yl-4′-hydroxybiphenyl-4-yl)-acrylic acid methyl ester (250 mg, 0.64 mmol) in DMF (2.5 ml) and the mixture was stirred at RT for 30 min. 4-(2-Chloroethyl)-morpholine hydrochloride (155 mg, 0.83 mmol) was added and the solution was heated to 60° C. for 14 h. The reaction was quenched by addition of water and was extracted with EtOAc. The organic layer was washed with a saturated solution of NaHCO3, water and brine, dried over Na2SO4 and evaporated under reduced pressure to obtain (E)-3-[3′-adamantan-1-yl-4′-(2-morpholin-4-yl-ethoxy)biphenyl-4-yl]-acrylic acid methyl ester (193 mg, 60%) after purification on silica gel (EtOAc:hexane 50:50).

1. temperaturethe solution was heated to 60° C. for 14 h
2. customThe reaction was quenched by addition of water
3. extractionwas extracted with EtOAc
4. washThe organic layer was washed with a saturated solution of NaHCO3, water and brine
5. dry with materialdried over Na2SO4
6. customevaporated under reduced pressure

ORD record

ord-9fe8e2e7bb804fca82c7cc1036f8b270

Source dataset

uspto-grants-2013_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08530517B2