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0 °C

9.2 ml (9.2 mmol, 1M in DCM) boron tribromide was added in drops at −50° C. to a solution of 399 mg (0.9 mmol) N-[(3-fluorophenyl)-methyl]-2-(2-methoxy-ethoxy)-4-methyl-7-(trifluoro-methyl)-quinoline-3-carboxylic acid amide (Example 7) in DCM (8 ml). The mixture was subsequently heated to 0° C. within 2 h and stirred for 1 h at 0° C. The mixture was then stirred for 1 h at 10° C. It was thereafter quenched with a 0.5 M aq. NaHCO3 sol. and diluted with MeOH and DCM. The organic phase was separated and washed with a 10%-strength aq. Na2S2O3 sol., dried over MgSO4 and concentrated in a vacuum. After crystallisation (EtOAc/hexane 1:1) of the residue, 109 mg (0.3 mmol, 29%) N-[(3-fluorophenyl)-methyl]-2-(2-hydroxy-ethoxy)-4-methyl-7-(trifluoromethyl)-quinoline-3-carboxylic acid amide (example 9) was obtained. MS: m/z 423.1 [M+H]+.

1. stirringThe mixture was then stirred for 1 h at 10° C
2. customIt was thereafter quenched with a 0.5 M aq. NaHCO3 sol.
3. additiondiluted with MeOH and DCM
4. customThe organic phase was separated
5. washwashed with a 10%-strength aq. Na2S2O3 sol.
6. dry with materialdried over MgSO4
7. concentrationconcentrated in a vacuum
8. customAfter crystallisation (EtOAc/hexane 1:1) of the residue