5-Amino-1-methyl-7-azaindole synthesis

Yield:883986-76-3 83%

Reaction Conditions:

with methanol;water;iron;ammonium chloride for 1 h;Heating / reflux;

Steps:

43.B

Step B: Synthesis of 5-amino-l-methyl-7-azaindole; [0223] A mixture of l-methyl-5-nitro-7-azaindole (0.152 g, 0.860 mmol), ammonium chloride (0.230 g, 4.30 mmol), iron powder (0.240 g, 4.30 mmol), methanol (10 mL), and water (10 mL) was heated at reflux for 1 h. After cooling to room temperature, the mixture was filtered and the filtrate extracted with ethyl acetate (3 x 50 mL). The organic layer was washed with brine (80 mL), dried over sodium sulfate, and concentrated. The crude product was purified by chromatography (silica, 50:50 ethyl acetate/hexanes) to give 5 -amino- 1- methyl-7-azaindole (0.105 g, 83%) as a brown oil: ¹H NMR (300 MHz, CDCl₃) δ 7.93 (d, J = 2.5 Hz, IH), 7.24 (d, J= 2.5 Hz, IH), 7.09 (d, J= 3.4 Hz, IH), 6.26 (d, J= 3.3 Hz, IH), 3.82 (s, 3H), 3.48 (br s, 2H).

References:

WO2009/42907,2009,A1 Location in patent:Page/Page column 88-89