Loading patent…
OwnerIvars Kalvinsh, Aleksandrs Chernobrovijs +2inventors
InventorsIvars Kalvinsh, Aleksandrs Chernobrovijs, Vyacheslav Tribulovich, Vladimir Labeish
Estimating the term…
A process for preparation of 6-[3-(1-adamantyl)-4-methoxyphenyl]-2-naphthoic acid from 2-(1-adamantyl)-4-bromanisolee is disclosed, based on transformation of 2-(1-adamantyl)-4-bromanisole into a Grignard's reagent by using metallic magnesium, anhydrous lithium chloride and dibromoethane followed by transmetallation with borates to 3-(adamantyl)-4-methoxyphenylboronic acid, which is converted into 6-[3-(1-adamantyl)-4-methoxyphenyl]-2-naphthoic acid esters by Suzuki-Miyaura cross-coupling reaction with alkyl-6-halonaftoates catalyzed by Pd [0] or Pd/phosphine ligands and followed by basic hydrolysis in ethylene glycol or 1,2-propanediol of ester thus obtained into 6-[3-(1-adamantyl)-4-methoxyphenyl]-2-naphthoic acid.
A process for manufacturing of 6-[3-(1-adamantyl)-4-methoxyphenyl]-2-naphtoic acid of formula (I)
The process of any claim from 2 to 5, wherein the inorganic base is selected from a group consisting of lithium, sodium, potassium and strontium carbonates, acetates and phosphates.
The process of any claim from 2 to 5, wherein the reaction is performed in the presence of organic solvents or mixture thereof or mixture of organic solvent with water.
The process of any claim of 2 to 7, wherein the palladium catalyst or Pd[0] and the compound of formula (IV) is used in a rate from 0.0005 to 0.1 mol of palladium catalyst to one mol of compound of formula (IV), preferably in a rate 0.005 mol to one mol.
The process of any claim of 2 to 8, wherein the reaction is performed at temperature from about 20° C. to about 100° C.
The process of any claim from 13 to 15, wherein the anhydrous inorganic lithium salt is selected from a group, consisting of anhydrous chloride, bromide, iodide, sulfate, perchlorate, tetrafluoroborate, preferably anhydrous lithium chloride.
The process of any claim from 13 to 16, wherein the anhydrous inorganic lithium salt is used in rate from 0.1 to 5.0 mol for one mol of compound (VI).
The process of any claim from 13 to 16, wherein the anhydrous inorganic lithium salt is used in the preferred rate from 1.2 to 1.5 mol for one mol of compound (VI).
The process of any claim from 2 to 9, wherein the compound of formula (IV) prepared by process of any claim from 10 to 18 is used without separation from the reaction mixture and purification.
Dependencies are inferred from the claim text.