N-[2-(4-bromophenyl)propan-2-yl]acetamide

Conditions: temp:45.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To 35 mg (0.16 mmol) 3-(4-cyclopropylmethoxy-phenoxy)-azetidine (IX.1) in THF (2.0 mL) are added under an argon atmosphere 41 mg (0.16 mmol) N-[1-(4-bromo-phenyl)-1-methyl-ethyl]-acetamide, 63 mg (0.64 mmol) NaOtBu, 19 mg (0.064 mmol) 2-(di-tert-butylphosphino)biphenyl and 15 mg (0.016 mmol) tris-(dibenzylidene-acetone)-dipalladium(0). The mixture is stirred for 12 h at 45° C. The mixture is filtered and concentrated in vacuo. The residue is purified by HPLC (Zorbax, acetronitrile/H2O (+0.15% HCOOH)) to yield the desired product. The mixture is filtered concentrated in vacuo The residue is purified by HPLC (Zorbax, acetronitrile/H2O (+0.15% HCOOH))

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

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

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

Conditions: temp:45.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To 35 mg (0.16 mmol) 3-(4-cyclopropylmethoxy-phenoxy)-azetidine (IX.1) in THF (2.0 mL) are added under an argon atmosphere 41 mg (0.16 mmol) N-[1-(4-bromo-phenyl)-1-methyl-ethyl]-acetamide, 63 mg (0.64 mmol) NaOtBu, 19 mg (0.064 mmol) 2-(di-tert-butylphosphino)biphenyl and 15 mg (0.016 mmol) tris-(dibenzylidene-acetone)-dipalladium(0). The mixture is stirred for 12 h at 45° C. The mixture is filtered and concentrated in vacuo. The residue is purified by HPLC (Zorbax, acetronitrile/H2O (+0.15% HCOOH)) to yield the desired product. The mixture is filtered concentrated in vacuo The residue is purified by HPLC (Zorbax, acetronitrile/H2O (+0.15% HCOOH))

Conditions: temp:45.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To 35 mg (0.16 mmol) 3-(4-cyclopropylmethoxy-phenoxy)-azetidine (IX.1) in THF (2.0 mL) are added under an argon atmosphere 41 mg (0.16 mmol) N-[1-(4-bromo-phenyl)-1-methyl-ethyl]-acetamide, 63 mg (0.64 mmol) NaOtBu, 19 mg (0.064 mmol) 2-(di-tert-butylphosphino)biphenyl and 15 mg (0.016 mmol) tris-(dibenzylidene-acetone)-dipalladium(0). The mixture is stirred for 12 h at 45° C. The mixture is filtered and concentrated in vacuo. The residue is purified by HPLC (Zorbax, acetronitrile/H2O (+0.15% HCOOH)) to yield the desired product. The mixture is filtered concentrated in vacuo The residue is purified by HPLC (Zorbax, acetronitrile/H2O (+0.15% HCOOH))

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

Procedure: To 21.0 g (97.6 mmol) 2-(4-bromophenyl)-propan-2-ol in 1 L ACN are added 16.1 mL conc. H2SO4 dropwise while keeping the temperature at 20° C. The resulting mixture is stirred at r.t. over night. The solvent is removed in vacuo and the residue is partitioned between water and diethylether. The organic layer is washed with water (2×), sat. aq. NaHCO3 solution (2×) and water again (1×). The solution is dried with MgSO4 and the solvent is removed in vacuo. The crude product is triturated with PE. at 20° C The solvent is removed in vacuo the residue is partitioned between water and diethylether The organic layer is washed with water (2×), sat. aq. NaHCO3 solution (2×) and water again (1×) The solution is dried with MgSO4 the solvent is removed in vacuo The crude product is triturated with PE