methyl 4-amino-5-cyano-2-methoxybenzoate

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

Procedure: To a solution of methyl 4-amino-5-cyano-2-methoxybenzoate (intermediate 129; 0.59 g, 2.88 mmol) in tetrahydrofuran (40 mL) was added dropwise lithium tetrahydroborate 2M (21.7 mL, 43.4 mmol) at 0° C. under nitrogen atmosphere. After 5 minutes was added dropwise ethanol (7.5 mL). The mixture was stirred for five days at room temperature. Then the crude was poured into a saturated solution of ammonium chloride and ice, and stirred for 10 minutes. The crude was extracted with ethyl acetate and washed with water and brine, dried and the solvent was removed under reduced pressure to obtain the title compound as a white solid (81%). stirred for 10 minutes The crude was extracted with ethyl acetate washed with water and brine dried the solvent was removed under reduced pressure

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

Procedure: To a solution of methyl 4-amino-5-cyano-2-methoxybenzoate (intermediate 129; 0.59 g, 2.88 mmol) in tetrahydrofuran (40 mL) was added dropwise lithium tetrahydroborate 2M (21.7 mL, 43.4 mmol) at 0° C. under nitrogen atmosphere. After 5 minutes was added dropwise ethanol (7.5 mL). The mixture was stirred for five days at room temperature. Then the crude was poured into a saturated solution of ammonium chloride and ice, and stirred for 10 minutes. The crude was extracted with ethyl acetate and washed with water and brine, dried and the solvent was removed under reduced pressure to obtain the title compound as a white solid (81%). stirred for 10 minutes The crude was extracted with ethyl acetate washed with water and brine dried the solvent was removed under reduced pressure

Conditions: temp:80.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A solution of methyl 4-amino-5-iodo-2-methoxybenzoate (intermediate 128; 5 g, 16.28 mmol) and dicyanozinc (1.5 g, 12.77 mmol) in dimethylformamide (50 mL) in a slenck vessel was degasified with nitrogen. Then tetrakis (1 g, 0.87 mmol) was added and the reaction mixture was stirred at 80° C. for 2 hours. Water was added into the reaction mixture and the crude was extracted with ethyl acetate, the organic layer was washed with brine, dried and the solvent was removed under reduced pressure. The crude obtained was treated with methanol and ether to obtain the title compound as a yellow solid (76%). the crude was extracted with ethyl acetate the organic layer was washed with brine dried the solvent was removed under reduced pressure The crude obtained

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

Procedure: To a solution of methyl 4-amino-5-cyano-2-methoxybenzoate (intermediate 129; 0.59 g, 2.88 mmol) in tetrahydrofuran (40 mL) was added dropwise lithium tetrahydroborate 2M (21.7 mL, 43.4 mmol) at 0° C. under nitrogen atmosphere. After 5 minutes was added dropwise ethanol (7.5 mL). The mixture was stirred for five days at room temperature. Then the crude was poured into a saturated solution of ammonium chloride and ice, and stirred for 10 minutes. The crude was extracted with ethyl acetate and washed with water and brine, dried and the solvent was removed under reduced pressure to obtain the title compound as a white solid (81%). stirred for 10 minutes The crude was extracted with ethyl acetate washed with water and brine dried the solvent was removed under reduced pressure

Conditions: temp:80.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A solution of methyl 4-amino-5-iodo-2-methoxybenzoate (intermediate 128; 5 g, 16.28 mmol) and dicyanozinc (1.5 g, 12.77 mmol) in dimethylformamide (50 mL) in a slenck vessel was degasified with nitrogen. Then tetrakis (1 g, 0.87 mmol) was added and the reaction mixture was stirred at 80° C. for 2 hours. Water was added into the reaction mixture and the crude was extracted with ethyl acetate, the organic layer was washed with brine, dried and the solvent was removed under reduced pressure. The crude obtained was treated with methanol and ether to obtain the title compound as a yellow solid (76%). the crude was extracted with ethyl acetate the organic layer was washed with brine dried the solvent was removed under reduced pressure The crude obtained