5-bromo-2-[2-(dimethylamino)ethoxy]aniline

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

Procedure: Using similar reaction conditions as described in step i of intermediate 17, 5-bromo-2-(2-(dimethylamino)ethoxy)aniline (1.8 g, 6.94 mmol) was mesylated with methanesulfonyl chloride (875 mg, 7.63 mol), pyridine (822 mg, 10.4 mmol), DCM (20 mL) to afford 1.97 g (83.12% yield) of the titled compound. 1H NMR (CDCl3, 300 MHz): δ 7.71-7.0 (d, 1H), 7.2-7.16 (dd, 1H), 6.92-6.89 (d, 1H), 4.07-4.04 (t, 2H), 2.92 (s, 3H), 2.56-2.53 (t, 2H), 2.35 (s, 6H). reaction conditions

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

Procedure: Zinc dust (4.52 g, 69.2 mmol) was added to a stirred solution of 2-(4-bromo-2-nitrophenoxy)-N,N-dimethylethanamine (4 g, 13.8 mmol), ammonium chloride (3.7 g, 69.2 mmol), THF/Water (40/40 mL) at RT. Reaction completed in 4 hours. The RM was filtered and the filtrate was concentrated. The residue was dissolved in ethyl acetate and washed with water, dried over sodium sulfate, concentrated to get the crude mass which was washed with hexanes to afford titled compound 1.85 g (51.67% yield) as solid. 1H NMR (DMSO-d6, 300 MHz): δ 6.74-6.70 (m, 2H), 6.59-6.56 (m, 1H), 4.99 (s, 2H), 3.97-3.93 (t, 2H), 2.59-2.56 (t, 2H), 2.18 (s, 6H). LCMS: m/z=260.8 (M+2). Reaction The RM was filtered the filtrate was concentrated The residue was dissolved in ethyl acetate washed with water dried over sodium sulfate concentrated to get the crude mass which was washed with hexanes

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

Procedure: Zinc dust (4.52 g, 69.2 mmol) was added to a stirred solution of 2-(4-bromo-2-nitrophenoxy)-N,N-dimethylethanamine (4 g, 13.8 mmol), ammonium chloride (3.7 g, 69.2 mmol), THF/Water (40/40 mL) at RT. Reaction completed in 4 hours. The RM was filtered and the filtrate was concentrated. The residue was dissolved in ethyl acetate and washed with water, dried over sodium sulfate, concentrated to get the crude mass which was washed with hexanes to afford titled compound 1.85 g (51.67% yield) as solid. 1H NMR (DMSO-d6, 300 MHz): δ 6.74-6.70 (m, 2H), 6.59-6.56 (m, 1H), 4.99 (s, 2H), 3.97-3.93 (t, 2H), 2.59-2.56 (t, 2H), 2.18 (s, 6H). LCMS: m/z=260.8 (M+2). Reaction The RM was filtered the filtrate was concentrated The residue was dissolved in ethyl acetate washed with water dried over sodium sulfate concentrated to get the crude mass which was washed with hexanes

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

Procedure: Using similar reaction conditions as described in step i of intermediate 17, 5-bromo-2-(2-(dimethylamino)ethoxy)aniline (1.8 g, 6.94 mmol) was mesylated with methanesulfonyl chloride (875 mg, 7.63 mol), pyridine (822 mg, 10.4 mmol), DCM (20 mL) to afford 1.97 g (83.12% yield) of the titled compound. 1H NMR (CDCl3, 300 MHz): δ 7.71-7.0 (d, 1H), 7.2-7.16 (dd, 1H), 6.92-6.89 (d, 1H), 4.07-4.04 (t, 2H), 2.92 (s, 3H), 2.56-2.53 (t, 2H), 2.35 (s, 6H). reaction conditions

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

Procedure: Zinc dust (4.52 g, 69.2 mmol) was added to a stirred solution of 2-(4-bromo-2-nitrophenoxy)-N,N-dimethylethanamine (4 g, 13.8 mmol), ammonium chloride (3.7 g, 69.2 mmol), THF/Water (40/40 mL) at RT. Reaction completed in 4 hours. The RM was filtered and the filtrate was concentrated. The residue was dissolved in ethyl acetate and washed with water, dried over sodium sulfate, concentrated to get the crude mass which was washed with hexanes to afford titled compound 1.85 g (51.67% yield) as solid. 1H NMR (DMSO-d6, 300 MHz): δ 6.74-6.70 (m, 2H), 6.59-6.56 (m, 1H), 4.99 (s, 2H), 3.97-3.93 (t, 2H), 2.59-2.56 (t, 2H), 2.18 (s, 6H). LCMS: m/z=260.8 (M+2). Reaction The RM was filtered the filtrate was concentrated The residue was dissolved in ethyl acetate washed with water dried over sodium sulfate concentrated to get the crude mass which was washed with hexanes