(4-amino-5-fluoro-2-methoxyphenyl)methanol

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of (4-amino-5-fluoro-2-methoxyphenyl)methanol (intermediate 91; 1.49 g, 8.7 mmol) in tetrahydrofuran (117 mL) was added dimethylaminopiridine (0.1 g, 0.81 mmol) and triethylamine (3.4 mL, 24.3 mmol). Then the mixture was cooled to 0° C. and tert-butylchlorodimethylsilane (2.45 g, 16.2 mmol) was added under argon atmosphere. The mixture was stirred 2 hours at room temperature. The solvent was removed under reduced pressure and the crude obtained was purified by column chromatography with silica gel, eluting with hexane/ether (from 0% to 100%). The title compound was obtained as an pale-orange solid (82%). The solvent was removed under reduced pressure the crude obtained was purified by column chromatography with silica gel eluting with hexane/ether (from 0% to 100%)

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of (4-amino-5-fluoro-2-methoxyphenyl)methanol (intermediate 91; 1.49 g, 8.7 mmol) in tetrahydrofuran (117 mL) was added dimethylaminopiridine (0.1 g, 0.81 mmol) and triethylamine (3.4 mL, 24.3 mmol). Then the mixture was cooled to 0° C. and tert-butylchlorodimethylsilane (2.45 g, 16.2 mmol) was added under argon atmosphere. The mixture was stirred 2 hours at room temperature. The solvent was removed under reduced pressure and the crude obtained was purified by column chromatography with silica gel, eluting with hexane/ether (from 0% to 100%). The title compound was obtained as an pale-orange solid (82%). The solvent was removed under reduced pressure the crude obtained was purified by column chromatography with silica gel eluting with hexane/ether (from 0% to 100%)