1-(bromomethyl)-2-butoxybenzene

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 2,6-Difluoro-N-1H-pyrazol-3-ylbenzamide (for a preparation see Intermediate 9)(89 mg, 0.40 mmol), potassium carbonate (83 mg, 0.60 mmol) and 1-(bromomethyl)-2-(butyloxy)benzene (for a preparation see Intermediate 2)(114 mg, 0.47 mmol) were weighed into a vial with a stirrer. N,N-dimethylformamide (1 ml) was added, the vial was capped and the mixture was stirred at room temperature for 28 h. The reaction mixture was filtered (hydrophobic frit), washing with MeOH to give a total volume of 2 ml. This solution was purified by MDAP (Sunfire column, formic acid buffer) (Method B). The solvent was removed to give the title compound as a colourless solid (9.4 mg); LCMS: (System 4) MH+=386, tRET=3.17 min. the vial was capped The reaction mixture was filtered (hydrophobic frit) washing with MeOH to give a total volume of 2 ml This solution was purified by MDAP (Sunfire column, formic acid buffer) (Method B) The solvent was removed

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 2,6-Difluoro-N-1H-pyrazol-4-ylbenzamide (for a preparation see intermediate 2, 45 mg, 0.20 mmol), 1-(bromomethyl)-2-(butyloxy)benzene (for a preparation see intermediate 4, 56 mg, 0.23 mmol) and potassium carbonate (42 mg, 0.30 mmol) were weighed into a vial with a stirrer. DMF (0.5 ml) was added, the vial was capped and the mixture was stirred at ambient temperature for 26 h. The reaction mixture was filtered, washing with MeOH to give a total volume of 1 ml. This solution was purified by MDAP Sunfire C18 column (Method B) using acetonitrile-water with a formic acid modifier. The solvent was removed to give the title compound (25 mg) as a colourless gum; LCMS (System 4): MH+=386, tRET=3.02 min. the vial was capped The reaction mixture was filtered washing with MeOH to give a total volume of 1 ml This solution was purified by MDAP Sunfire C18 column (Method B) The solvent was removed