4-fluoro-2-N-methylbenzene-1,2-diamine

Conditions: temp:120.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of 5-methoxypyridine-3-carbaldehyde (0.052 g, 0.378 mmol) in DMF (1.89 mL) were added the title compound from Example 1 Step B (0.053 g, 0.38 mmol) and Na2S2O5 (0.288 g, 1.51 mmol). The resulting mixture was stirred at 120° C. overnight, then cooled to room temperature and diluted with water and ethyl acetate. The organic layer was separated, washed with water and brine, dried over magnesium sulfate, filtered, and concentrated. Purification by flash chromatography on silica gel (50% ethyl acetate in hexanes, then 100% ethyl acetate) provided the title compound: LCMS m/z 258.17 [M+H]+; 1H NMR (500 MHz, CDCl3) δ 8.56 (d, J=1.6 Hz, 1 H), 8.46 (d, J=2.9 Hz, 1 H), 7.66 (dd, J=8.6, 4.8 Hz, 1 H), 7.65 (t, J=2.1, 2.1 Hz, 1 H), 7.12-7.06 (m, 2 H), 3.95 (s, 3 H), 3.88 (s, 3 H). cooled to room temperature The organic layer was separated washed with water and brine dried over magnesium sulfate filtered concentrated Purification by flash chromatography on silica gel (50% ethyl acetate in hexanes

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

Procedure: To the title compound from Example 1 Step A (0.267 g, 1.57 mmol) were added palladium on carbon (0.027 g) and methanol (7.85 mL). The resulting mixture was stirred under an atmosphere of hydrogen at room temperature overnight. The mixture was then filtered through CELITE® using dichloromethane, and the filtrate was concentrated. Purification by flash chromatography (50% ethyl acetate in hexanes, then 100% ethyl acetate) provided the title compound: 1H NMR (500 MHz, CDCl3) δ 6.61 (dd, J=8.2, 5.6 Hz, 1 H), 6.36-6.30 (m, 2 H), 3.22 (br s, 3 H), 2.84 (s, 3 H). The mixture was then filtered through CELITE® the filtrate was concentrated Purification by flash chromatography (50% ethyl acetate in hexanes

Conditions: temp:120.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of 5-methoxypyridine-3-carbaldehyde (0.052 g, 0.378 mmol) in DMF (1.89 mL) were added the title compound from Example 1 Step B (0.053 g, 0.38 mmol) and Na2S2O5 (0.288 g, 1.51 mmol). The resulting mixture was stirred at 120° C. overnight, then cooled to room temperature and diluted with water and ethyl acetate. The organic layer was separated, washed with water and brine, dried over magnesium sulfate, filtered, and concentrated. Purification by flash chromatography on silica gel (50% ethyl acetate in hexanes, then 100% ethyl acetate) provided the title compound: LCMS m/z 258.17 [M+H]+; 1H NMR (500 MHz, CDCl3) δ 8.56 (d, J=1.6 Hz, 1 H), 8.46 (d, J=2.9 Hz, 1 H), 7.66 (dd, J=8.6, 4.8 Hz, 1 H), 7.65 (t, J=2.1, 2.1 Hz, 1 H), 7.12-7.06 (m, 2 H), 3.95 (s, 3 H), 3.88 (s, 3 H). cooled to room temperature The organic layer was separated washed with water and brine dried over magnesium sulfate filtered concentrated Purification by flash chromatography on silica gel (50% ethyl acetate in hexanes

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

Procedure: To the title compound from Example 1 Step A (0.267 g, 1.57 mmol) were added palladium on carbon (0.027 g) and methanol (7.85 mL). The resulting mixture was stirred under an atmosphere of hydrogen at room temperature overnight. The mixture was then filtered through CELITE® using dichloromethane, and the filtrate was concentrated. Purification by flash chromatography (50% ethyl acetate in hexanes, then 100% ethyl acetate) provided the title compound: 1H NMR (500 MHz, CDCl3) δ 6.61 (dd, J=8.2, 5.6 Hz, 1 H), 6.36-6.30 (m, 2 H), 3.22 (br s, 3 H), 2.84 (s, 3 H). The mixture was then filtered through CELITE® the filtrate was concentrated Purification by flash chromatography (50% ethyl acetate in hexanes