[(E)-pent-1-enyl]boronic acid

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

Procedure: To a solution of 2-(2-iodo-3-methyl-benzoylamino)-indan-2-carboxylic acid ethyl ester (200 mg, 0.45 mmol) and trans-1-penten-1-ylboronic acid (205 mg, 1.80 mmol) in EtOH (10 mL) and dioxane (10 mL) is added palladium anchored homogeneous catalyst, FibreCatPd(0) (4.84% Pd, 96 mg, 0.045 mmol) and 2M aqueous solution of K2SO4 (0.90 mL, 1.80 mmol). The resulting reaction mixture is covered with argon and run in a microwave reaction: 110° C., 8 h. After concentration in vacuo, the residue is purified by HPLC to give a pure product (145) as white solid (107 mg, 60%). The resulting reaction mixture run in a microwave reaction 110° C., 8 h After concentration in vacuo the residue is purified by HPLC

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

Procedure: 5-{3-[2-(4-Bromo-benzyl)-4-(2,4-dichloro-phenyl)-imidazol-1-yl]-phenyl}-1,2,5-thiadiazolidine-3-one-1,1-dioxide (59 mg, 0.1 mmol) was treated as described in general procedure G using trans-1-penten-1-ylboronic acid (34 mg, 0.3 mmol) to give 5-{3-[4-(2,4-dichloro-phenyl)-2-(4-pent-1-enyl-benzyl)-imidazol-1-yl]-phenyl}-1,2,5-thiadiazolidine-3-one-1,1-dioxide.

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

Procedure: A solution of 11 (0.10 g, 0.19 mmol), E-penten-1-ylboronic acid (44.0 mg, 0.38 mmol), tetrakis(triphenylphosphine)palladium (22.0 mg, 0.023 mmol), and NaHCO3 (41.0 mg, 0.38 mmol) in 1:1 DME/H2O (3 mL) was heated at 100° C. for 1 h. The reaction was allowed to cool to room temperature, diluted with H2O, extracted with EtOAc, dried (Na2SO4), filtered, and concentrated. Chromatography (SiO2, 3:1 Hex/EtOAc) gave 12 (43.0 mg, 51%) as a colorless film. extracted with EtOAc dried (Na2SO4) filtered concentrated

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

Procedure: Prepared from the product of step A (example 16) and (E)-1-penteneboronic acid according to general procedure 2. The free base was converted to the HCl salt with 2N HCl in Et2O to provide the title compound (58 mg, 55%) as a brown solid; 1H NMR (500 MHz, CD3OD) δ 7.65 (d, J=9.7 Hz, 1H), 7.56 (s, 1H), 6.77-6.63 (m, 3H), 3.91-3.89 (m, 4H), 3.54 (t, J=6.4 Hz, 2H), 3.24-3.21 (m, 6H), 2.27 (q, J=6.8 Hz, 2H), 2.20-2.14 (m, 2H), 1.58-1.51 (m, 2H), 0.98 (t, J=7.4 Hz, 3H); 13C NMR (125 MHz, CD3OD) δ 155.6, 136.8, 134.2, 129.2, 126.4, 124.8, 116.4, 115.0, 65.4, 57.0, 53.5, 39.8, 36.8, 24.4, 23.7, 14.1; HPLC tR=9.3 min (Synergi), 97.3%; ES-MS: (M+H)=330 m/z.

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

Procedure: To a solution of 2-(2-iodo-3-methyl-benzoylamino)-indan-2-carboxylic acid ethyl ester (200 mg, 0.45 mmol) and trans-1-penten-1-ylboronic acid (205 mg, 1.80 mmol) in EtOH (10 mL) and dioxane (10 mL) is added palladium anchored homogeneous catalyst, FibreCatPd(0) (4.84% Pd, 96 mg, 0.045 mmol) and 2M aqueous solution of K2SO4 (0.90 mL, 1.80 mmol). The resulting reaction mixture is covered with argon and run in a microwave reaction: 110° C., 8 h. After concentration in vacuo, the residue is purified by HPLC to give a pure product (145) as white solid (107 mg, 60%). The resulting reaction mixture run in a microwave reaction 110° C., 8 h After concentration in vacuo the residue is purified by HPLC