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US 2010/0076219 A1Published application
Method for preparation of 6-[3(1-adamantyl) -4-methoxyphenyl]-2-naphtoic acid
AssigneeJSC Grindeks
InventorsIvars Kalvinsh, Aleksandrs Chernobrovijs, Vyacheslav Tribulovich, Vladimir Labeish
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Abstract
A method for preparation of 6-[3-(1-adamantyl)-4-methoxyphenyl]-2-naphthoic acid is disclosed based on “one pot” synthesis approach including a direct synthesis of boronic acid derivative from 2-(1-adamantyl)-4-bromoanisole and cycloboranes with a subsequent Suzuki-Miyaura coupling with 6-halonaphthenoates and basic hydrolysis of the reaction product in ethylene glycol or 1,2-propanediol.
Claims15
1-12. (canceled)
A method for preparation of a compound of formula (I)
- wherein:
- R1 is selected from the group consisting of K, Na, Li, H, straight C1-C10alkyl, branched C3-C10alkyl or cyclicC3-C10alkyl and CH2OC1-C5alkyl,
- from a compound of formula (II)
- wherein:
- is Hal is selected from the group consisting of Cl, Br and I,
- by reacting with a compound of formula (III)
- wherein:
- R1 and R2 independently of each other are selected from the group consisting of K, Na, Li, H, aryl, straight C1-C10alkyl, branched C3-C10alkyl and cyclic C3-C10alkyl, or R1 and R2 together form a group (CR4R5)m—(CR6R7)n—, wherein R4, R5, R6 and R7 independently of each other are selected from the group consisting of aryl, H, straight C1-C5alkyl, branched C3-C5alkyl and cyclic C3-C5alkyl;
- and m and n independently of each other are 1 or 2,
- or R1 and R2 together form ortho-substituted aryl,
- R3 is selected from the group consisting of no H and
- in an inert solvent in presence of a basic agent and a catalyst selected from the group consisting of a palladium catalyst, Pd(0) and Pd(0)-phosphine ligand complex, with further reacting the product thus obtained with a compound (IV)
- wherein:
- R9 is selected from the group consisting of K, Na, Li, H, aryl, straight C1-C10alkyl, branched C3-C10alkyl, cyclic C3-C10alkyl, and CH2OC1-C5alkyl;
- Hal is selected from the group consisting Cl, Br and I, in the same reaction mixture, with or without addition of an inorganic base.
12 more elements
Dependencies are inferred from the claim text.