Process for preparing heteroaryl and unsaturated heterocycloalkylmagnesium reagents and uses thereof

A process of preparing a nucleophilic heteroaryl or unsaturated heterocycloalkylmagnesium reagent comprising reacting a compound of formula (I):

• 40
• wherein:
• X is —O— or —S—;
• Y is nitrogen or —CR3a—;
• Y′ is nitrogen or —CR2a— provided that Y and Y′ are not simultaneously nitrogen;
• one of R2 and R3 is hydrogen, (C1-6)alkyl, (C1-6)alkoxy, (C1-6)alkoxy(C1-6)alkyl, (C1-6)alkylthio, (C5-6)cycloalkyl, (C5-6)cycloalkylalkyl, halo, nitro, halo(C1-3)alkyl, (C6-12)aryl, heteroaryl, heterocycloalkyl, (C6-12)aryl(C1-6)alkyl, heteroaryl(C1-6)alkyl, (C1-6)alkylsulfonyl, (C6-12)arylsulfonyl, (C6-12)aryl(C1-6)alkylsulfonyl, heteroarylsulfonyl, heteroaryl (C1-6)-alkylsulfonyl, aminosulfonyl, (C1-6)alkylaminosulfonyl, (C1-6)dialkylaminosulfonyl, —CONR4R5 (where R4 and R5 are independently of each other hydrogen, (C1-6)alkyl, (C1-6)alkoxy, aryl, aryl(C1-6)alkyl, heteroaryl, heteroaryl(C1-6)alkyl, (C5-6)cycloalkyl, (C5-6)cycloalkyl(C1-6)alkyl, heterocycloalkyl, or heterocycloalkyl(C1-6)alkyl, or R4 and R5 together with the nitrogen atom to which they are attached form heterocycloamino), —NHCOR6 (where R6 is (C1-6)alkyl, (C6-12)aryl, aryl(C1-6)alkyl, heteroaryl, heteroaryl (C1-6)alkyl, (C5-6)cycloalkyl, (C5-6)cycloalkyl(C1-6)alkyl, heterocycloalkyl, or heterocycloalkyl(C1-6)alkyl), —SO2NR7R8 (where R7 and R8 are independently of each other hydrogen, (C1-6)alkyl, (C6-12)aryl, (C6-12)aryl(C1-6)alkyl, heteroaryl, heteroarylalkyl, (C5-6)cycloalkyl, (C5-6)cycloalkyl(C1-6)alkyl, heterocycloalkyl, or heterocycloalkyl(C1-6)alkyl, or R7 and R8 together with the nitrogen atom to which they are attached form heterocycloamino), -alkylene-CONR4R5 (where R4 and R5 are as defined above), -alkylene-NHCOR6 (where R6 is as defined above), or -alkylene-SO2NR7R8 (where R7 and R8 are as defined above);
• and
• the other of R2 and R3 is hydrogen or (C1-6)alkyl wherein within R2 or R3 said aryl, heteroaryl, or heterocycloalkyl is optionally substituted further with one, two, or three substituents independently selected from the group consisting of (C1-6)alkoxy, (C1-6)alkyl, (C6-12)aryl(C1-6)alkyl, halo, nitro, and halo(C1-3)alkyl;
• or
• when Y and Y′ are carbon, then R2 and R3 together with the atoms to which they are attached form an optionally substituted benzene, napthyl, (C3-6)cycloalkyl, or an aromatic or non-aromatic heterocyclic ring;
• R2a and R3a are independently hydrogen or alkyl;
• or R2a and R3a together form a covalent bond, provided that when Y or Y′ is nitrogen, R2a and R3 or R2 and R3a together form a covalent bond;
• with a Grignard reagent provided that (I) is not 1,2,4- or 1,3,4-oxadiazole.