Process for the manufacture of organic compounds

A process for the manufacture of a compound of formula (I), or salt thereof,

• comprising
• reacting a compound of formula (V), or salt thereof,
• wherein R is C1-7alkyl,
• wherein R1 is hydrogen, C1-7alkyl, C1-7alkoxy, C3-8cycloalkyl or C8-10aryl, each unsubstituted or substituted by one or more, e.g. up to three, substituents selected from, halo, nitro, C1-7alkyl, halo-C1-7alkyl, C1-7alkoxy-C1-7alkyl, C1-7alkoxy, halo-C1-7alkoxy, C1-7alkoxy-C1-7alkoxy, halo-C1-7alkoxy-C1-7alkoxy, C1-7alkyl-C1-7alkoxy, halo-C1-7alkyl-C1-7alkoxy;
• and
• R2, R3 and R4 are the same or different form each other and are hydrogen, halo, nitro, C1-7alkyl, C1-7alkoxy, C3-8cycloalkyl or C8-10aryl, each unsubstituted or substituted by one or more, e.g. up to three, substituents selected from, halo, nitro, C1-7alkyl, halo-C1-7alkyl, C1-7alkoxy-C1-7alkyl, C1-7alkoxy, halo-C1-7alkoxy, C1-7alkoxy-C1-7alkoxy, halo-C1-7alkoxy-C1-7alkoxy, C1-7alkyl-C1-7alkoxy, halo-C1-7alkyl-C1-7alkoxy;
• with an organoaluminium halide of formula R5R6AlX or R5AlX2
• wherein R5 and R6 are, independently from one another, C1-7alkyl, C3-C8alkenyl, C3-8cycloalkyl or C6-10aryl, preferably C1-7alkyl, and X is halogen,
• to obtain the compound of formula (I).

A step-wise process for the manufacture of a compound of formula (I), or salt thereof,

• comprising the steps of
• i) reacting a compound of formula (III), or salt thereof,
• wherein R is C1-7alkyl,
• wherein R1 is hydrogen, C1-7alkyl, C1-7alkoxy, C3-8cycloalkyl or C6-10aryl, each unsubstituted or substituted by one or more, e.g. up to three, substituents selected from, halo, nitro, C1-7alkyl, halo-C1-7alkyl, C1-7alkoxy-C1-7alkyl, C1-7alkoxy, halo-C1-7alkoxy, C1-7alkoxy-C1-7alkoxy, halo-C1-7alkoxy-C1-7alkoxy, C1-7alkyl-C1-7alkoxy, halo-C1-7alkyl-C1-7alkoxy;
• and
• R2, R3 and R4 are the same or different form each other and are hydrogen, halo, nitro, C1-7alkyl, C1-7alkoxy, C3-8cycloalkyl or C6-10aryl, each unsubstituted or substituted by one or more, e.g. up to three, substituents selected from, halo, nitro, C1-7alkyl, halo-C1-7alkyl, C1-7alkoxy-C1-7alkyl, C1-7alkoxy, halo-C1-7alkoxy, C1-7alkoxy-C1-7alkoxy, halo-C1-7alkoxy-C1-7alkoxy, C1-7alkyl-C1-7alkoxy, halo-C1-7alkyl-C1-7alkoxy;
• with an organoaluminium halide of formula R5R6AlX or R5AlX2
• wherein R5 and R6 are, independently from one another, C1-7alkyl, C3-C8alkenyl, C3-8cycloalkyl or C6-10aryl, preferably C1-7alkyl, and X is halogen,
• to obtain the compound of formula (IV), or salt thereof,
• such as an amine salt thereof,
• ii) treating the compound of formula (IV), or salt thereof,
• such as an amine salt thereof,
• with an azide reagent to provide compound of formula (I).

A one-pot process for the manufacture of a compound of formula (I), or salt thereof,

• comprising
• i) reacting a compound of formula (III), or salt thereof,
• wherein R is C1-7alkyl,
• wherein R1 is hydrogen, C1-7alkyl, C1-7alkoxy, C3-8cycloalkyl or C6-10aryl, each unsubstituted or substituted by one or more, e.g. up to three, substituents selected from, halo, nitro, C1-7alkyl, halo-C1-7alkyl, C1-7alkoxy-C1-7alkyl, C1-7alkoxy, halo-C1-7alkoxy, C1-7alkoxy-C1-7alkoxy, halo-C1-7alkoxy-C1-7alkoxy, C1-7alkyl-C1-7alkoxy, halo-C1-7alkyl-C1-7alkoxy;
• and
• R2, R3 and R4 are the same or different form each other and are hydrogen, halo, nitro, C1-7alkyl, C1-7alkoxy, C3-8cycloalkyl or C6-10aryl, each unsubstituted or substituted by one or more, e.g. up to three, substituents selected from, halo, nitro, C1-7alkyl, halo-C1-7alkyl, C1-7alkoxy-C1-7alkyl, C1-7alkoxy, halo-C1-7alkoxy, C1-7alkoxy-C1-7alkoxy, halo-C1-7alkoxy-C1-7alkoxy, C1-7alkyl-C1-7alkoxy, halo-C1-7alkyl-C1-7alkoxy;
• with an organoaluminium halide of formula R5R6AlX or R5AlX2
• wherein R5 and R6 are, independently from one another, C1-7alkyl, C3-C8alkenyl, C3-8cycloalkyl or C6-10aryl, preferably C1-7alkyl, and X is halogen,
• to obtain the compound of formula (IV), or salt thereof,
• such as an amine salt thereof,
• ii) adding to the resulting reaction mixture of step i) an azide reagent
• to obtain the compound of formula (I).