2-(4-bromophenyl)-N-methylethanamine

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: Benzyl chloroformate (0.97 mL, 6.7 mmol) was added dropwise to a solution of 23B (1.1 g, 5.1 mmol)in CH2Cl2 (26 mL) and triethylamine (1 mL, 7.5 mmol). The reaction mixture washed with brine, dried over Na2SO4 and concentrated in vacuo. Purification by flash chromatography (0% to 50% EtOAc in hexanes) afforded 28C (1.15 g, 65%) as a clear oil. 1H NMR (400 MHz, CDCl3) δ ppm 2.70-2.94 (m, 5 H) 3.47 (m, 2 H) 5.08 (m, 2 H) 6.90-7.12 (m, 2 H) 7.26-7.44 (m, 7 H). The reaction mixture washed with brine dried over Na2SO4 concentrated in vacuo Purification by flash chromatography (0% to 50% EtOAc in hexanes)

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

Procedure: Benzyl chloroformate (0.97 mL, 6.7 mmol) was added dropwise to a solution of 23B (1.1 g, 5.1 mmol)in CH2Cl2 (26 mL) and triethylamine (1 mL, 7.5 mmol). The reaction mixture washed with brine, dried over Na2SO4 and concentrated in vacuo. Purification by flash chromatography (0% to 50% EtOAc in hexanes) afforded 28C (1.15 g, 65%) as a clear oil. 1H NMR (400 MHz, CDCl3) δ ppm 2.70-2.94 (m, 5 H) 3.47 (m, 2 H) 5.08 (m, 2 H) 6.90-7.12 (m, 2 H) 7.26-7.44 (m, 7 H). The reaction mixture washed with brine dried over Na2SO4 concentrated in vacuo Purification by flash chromatography (0% to 50% EtOAc in hexanes)

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

Procedure: A solution of 25A (750 mg, 2.3 mmol) and 23B (486 mg, 4.5 mmol) with potassium carbonate (627 mg, 2.3 mmol) in DMF (6 mL) were heated at 50° C. for 15 h. The mixture was diluted with water (100 mL) and extracted with EtOAc (3×100 mL). The organics were washed with brine, dried over Na2SO4 and concentrated. The crude product was purified by flash chromatography (0% to 100% EtOAc in hexanes) to yield give 25B (950 mg, 93%) as a colorless oil. MS (ESI) m/z 449.89/451.91 (M+H)+. extracted with EtOAc (3×100 mL) The organics were washed with brine dried over Na2SO4 concentrated The crude product was purified by flash chromatography (0% to 100% EtOAc in hexanes) to yield

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

Procedure: Using a procedure analogous to that used to prepare 22C, 23B (300 mg, 1.4 mmol) was reacted with 3-isocyanatobenzonitrile to yield 23C (406 g, 81%) as a clear oil. MS (ESI) m/z 358.31/360.29 (M+H)+.

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

Procedure: Using a procedure analogous to that used to prepare 22B, 23A (1.6 g, 7.0 mmol) was reduced with borane in THF to yield 23B (1.45 g, 97%) as a clear oil. MS (ESI) m/z 214.22/216.22 (M+H)+.

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

Procedure: Using a procedure analogous to that used to prepare 22B, 23A (1.6 g, 7.0 mmol) was reduced with borane in THF to yield 23B (1.45 g, 97%) as a clear oil. MS (ESI) m/z 214.22/216.22 (M+H)+.

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: Benzyl chloroformate (0.97 mL, 6.7 mmol) was added dropwise to a solution of 23B (1.1 g, 5.1 mmol)in CH2Cl2 (26 mL) and triethylamine (1 mL, 7.5 mmol). The reaction mixture washed with brine, dried over Na2SO4 and concentrated in vacuo. Purification by flash chromatography (0% to 50% EtOAc in hexanes) afforded 28C (1.15 g, 65%) as a clear oil. 1H NMR (400 MHz, CDCl3) δ ppm 2.70-2.94 (m, 5 H) 3.47 (m, 2 H) 5.08 (m, 2 H) 6.90-7.12 (m, 2 H) 7.26-7.44 (m, 7 H). The reaction mixture washed with brine dried over Na2SO4 concentrated in vacuo Purification by flash chromatography (0% to 50% EtOAc in hexanes)

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

Procedure: A solution of 25A (750 mg, 2.3 mmol) and 23B (486 mg, 4.5 mmol) with potassium carbonate (627 mg, 2.3 mmol) in DMF (6 mL) were heated at 50° C. for 15 h. The mixture was diluted with water (100 mL) and extracted with EtOAc (3×100 mL). The organics were washed with brine, dried over Na2SO4 and concentrated. The crude product was purified by flash chromatography (0% to 100% EtOAc in hexanes) to yield give 25B (950 mg, 93%) as a colorless oil. MS (ESI) m/z 449.89/451.91 (M+H)+. extracted with EtOAc (3×100 mL) The organics were washed with brine dried over Na2SO4 concentrated The crude product was purified by flash chromatography (0% to 100% EtOAc in hexanes) to yield