Process for Synthesis of Intermediates Useful for Making Substituted Indazole and Azaindazole Compounds

• US 20110137042A1
• Filed: 12/01/2010
• Published: 06/09/2011
• Est. Priority Date: 12/08/2009
• Status: Abandoned Application

• Current Assignee: Boehringer Ingelheim International GmbH (C.H. Boehringer Sohn AG & Co. KG)
• Original Assignee: Boehringer Ingelheim International GmbH (C.H. Boehringer Sohn AG & Co. KG)
• Inventors: RODRIGUEZ, Sonia, REEVES, Jonathan Timothy, RAZAVI, Hossein
• Application Number:
  US12/957,483
• Publication Number:
  US 20110137042A1
• Time in Patent Office: Days
• US Class Current: 546/294
• CPC Class Codes: A61P 29/00 Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
• CPC Class Codes: C07D 213/71 to which a second hetero atom is attached

Abstract

Disclosed are processes for preparing compounds of formula (I):

the compounds are useful as intermediates for preparing indazole and azaindazole substituted compounds.

Claims

1. A process of making a compound of the formula (I):

2. The process according to claim 1 wherein:

the metal catalyst a Pd or Ni based catalyst;

the hydrogen is at pressures of 15-1000 psi,

the time is 7 hours;

the temperature is 25°

C.;

the acid is concentrated aqueous hydrochloric acid;

the solvent is chosen from methanol, ethanol, isopropanol and acetic acid;

the ionic salt is a hydrochloride.

3. The process according to claim 2 wherein:

the metal catalyst Palladium over Carbon;

the hydrogen is at pressures of 100-200 psi,

the solvent is methanol.

4. The process according to claim 3 wherein:

the metal catalyst 10% Palladium over Carbon, with water.

5. The process according to claim 4 wherein:

the metal catalyst 10% Palladium over Carbon, with 50% water.

6. The process according to any one of claims 1-5 wherein

the nitrile of formula (II) is on the 4 position:

7. The process according to claim 6 wherein R is C1-5 alkyl.

8. The process according to claim 6 wherein R is methyl.