5-bromo-2-methylaniline

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:0.00; pressure:0.00; stir:

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: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: To a solution of 4-(4-phenylquinazolin-2-ylamino)benzoyl chloride (1.0 g, 2.8 mmol) and Hunig's base (600 μL, 3.4 mmol) in tetrahydrofuran (25 mL) was added 5-bromo-2-methylaniline (600 mg, 3.2 mmol), and the reaction was allowed to stir at rt overnight. The mixture was concentrated on a rotary evaporator and purified by flash column chromatography to give N-(5-bromo-2-methylphenyl)-4-[(4-phenylquinazolin-2-yl)amino]benzamide (1.0 g, 70%) as a yellow solid. 1H NMR (400 MHz, DMSO-d6): δ 10.34 (s, 1H), 9.77 (s, 1H), 8.18 (d, 2), 7.98 (d, 2H), 7.82 (m, 6H), 7.65 (m, 4H), 7.41 (dt, 1H), 7.35 (dd, 1H), 7.25 (d, 1H), 2.24 (s, 3H). MS (EI) for C28H21BrN4O: 511.2 (MH+). The mixture was concentrated on a rotary evaporator purified by flash column chromatography

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

Procedure: Prepared by the method of Example 69a) using 5-bromo-2-methylaniline (2.60 g, Example 78a)), sodium nitrite (1.05 g), concentrated hydrochloric acid (20 ml), anhydrous magnesium chloride (2.6 g), acetic acid saturated with sulfur dioxide (50 ml) and containing copper (II) chloride (0.37 g). The normal work-up and subsequent treatment with ammonium hydroxide (50 ml) followed by the same work-up afforded the subtitle compound as a solid (0.42 g). Prepared by the method of Example 69a)

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

Procedure: A slurry of 5-bromo-2-methylnitrobenzene (3.00 g), iron powder (3.11 g), and ammonium chloride (2.97 g), in 3:1 ethanol : water (50 ml) was heated at reflux temperature for 1 hour. The mixture was poured into 10% aqueous sodium hydroxide and filtered through Celite®. The filtrate was then extracted with ethyl acetate, the extracts washed with brine, dried over magnesium sulfate, filtered and evaporated to afford the subtitle compound as an oil (2.64 g). at reflux temperature for 1 hour filtered through Celite® The filtrate was then extracted with ethyl acetate the extracts washed with brine dried over magnesium sulfate filtered evaporated