2-bromo-N-(cyclopropylmethyl)aniline

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

Procedure: A solution of 2-bromoaniline (1.720 g, 10.00 mmol), cyclopropanecarbaldehyde (0.374 mL, 5.00 mmol), and acetic acid (2.86 mL, 50.0 mmol) in dichloromethane (50 mL) was heated at 50° C. for 1 hour. The solution was cooled in an ice bath and sodium triacetoxyborohydride (2.119 g, 10.00 mmol) was added. This mixture was stirred for 2 hours while warming to ambient temperature and then partitioned between saturated sodium bicarbonate solution (100 mL) and ethyl acetate (100 mL). The organic layer was dried over anhydrous sodium sulfate, filtered, and concentrated. The residue was purified by flash column chromatography (silica gel, 0-10% ethyl acetate in heptane) to provide the title compound (1.05 g, 93% yield). The solution was cooled in an ice bath partitioned between saturated sodium bicarbonate solution (100 mL) and ethyl acetate (100 mL) The organic layer was dried over anhydrous sodium sulfate filtered concentrated The residue was purified by flash column chromatography (silica gel, 0-10% ethyl acetate in heptane)

Conditions: temp:50.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A 100 mL flask was charged with 2-bromoaniline (1.720 g, 10.00 mmol), cyclopropanecarbaldehyde (0.374 mL, 5.00 mmol), acetic acid (2.86 mL, 50.0 mmol) and dichloromethane (50 mL). The mixture was heated at 50° C. for 1 hour. The mixture was then cooled in an ice bath and the sodium triacetoxyborohydride (2.119 g, 10.00 mmol) was added in portionwise over a few minutes. After 15 minutes, the ice bath was removed and the mixture was stirred for 2 hours at ambient temperature. The reaction mixture was quenched with 2.5 M sodium hydroxide (16 mL) and then partitioned between saturated sodium bicarbonate solution (100 mL) and ethyl acetate (100 mL). The layers were separated and the organic layer was dried over anhydrous sodium sulfate, filtered, and concentrated. The mixture was then cooled in an ice bath the ice bath was removed The reaction mixture was quenched with 2.5 M sodium hydroxide (16 mL) partitioned between saturated sodium bicarbonate solution (100 mL) and ethyl acetate (100 mL) The layers were separated the organic layer was dried over anhydrous sodium sulfate filtered concentrated

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

Procedure: Example 142A was prepared as described in Example 111A substituting cyclopropanecarbaldehyde for Example 105B and 2-bromoaniline for tert-butyl piperidin-4-ylcarbamate. The isolated product was purified by flash chromatography (silica gel, 0-10% ethyl acetate in heptane) to give the title compound. Example 142A was prepared The isolated product was purified by flash chromatography (silica gel, 0-10% ethyl acetate in heptane)

Conditions: temp:50.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A 100 mL flask was charged with 2-bromoaniline (1.720 g, 10.00 mmol), cyclopropanecarbaldehyde (0.374 mL, 5.00 mmol), acetic acid (2.86 mL, 50.0 mmol) and dichloromethane (50 mL). The mixture was heated at 50° C. for 1 hour. The mixture was then cooled in an ice bath and the sodium triacetoxyborohydride (2.119 g, 10.00 mmol) was added in portionwise over a few minutes. After 15 minutes, the ice bath was removed and the mixture was stirred for 2 hours at ambient temperature. The reaction mixture was quenched with 2.5 M sodium hydroxide (16 mL) and then partitioned between saturated sodium bicarbonate solution (100 mL) and ethyl acetate (100 mL). The layers were separated and the organic layer was dried over anhydrous sodium sulfate, filtered, and concentrated. The mixture was then cooled in an ice bath the ice bath was removed The reaction mixture was quenched with 2.5 M sodium hydroxide (16 mL) partitioned between saturated sodium bicarbonate solution (100 mL) and ethyl acetate (100 mL) The layers were separated the organic layer was dried over anhydrous sodium sulfate filtered concentrated

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

Procedure: A solution of 2-bromoaniline (1.720 g, 10.00 mmol), cyclopropanecarbaldehyde (0.374 mL, 5.00 mmol), and acetic acid (2.86 mL, 50.0 mmol) in dichloromethane (50 mL) was heated at 50° C. for 1 hour. The solution was cooled in an ice bath and sodium triacetoxyborohydride (2.119 g, 10.00 mmol) was added. This mixture was stirred for 2 hours while warming to ambient temperature and then partitioned between saturated sodium bicarbonate solution (100 mL) and ethyl acetate (100 mL). The organic layer was dried over anhydrous sodium sulfate, filtered, and concentrated. The residue was purified by flash column chromatography (silica gel, 0-10% ethyl acetate in heptane) to provide the title compound (1.05 g, 93% yield). The solution was cooled in an ice bath partitioned between saturated sodium bicarbonate solution (100 mL) and ethyl acetate (100 mL) The organic layer was dried over anhydrous sodium sulfate filtered concentrated The residue was purified by flash column chromatography (silica gel, 0-10% ethyl acetate in heptane)

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

Procedure: Example 142A was prepared as described in Example 111A substituting cyclopropanecarbaldehyde for Example 105B and 2-bromoaniline for tert-butyl piperidin-4-ylcarbamate. The isolated product was purified by flash chromatography (silica gel, 0-10% ethyl acetate in heptane) to give the title compound. Example 142A was prepared The isolated product was purified by flash chromatography (silica gel, 0-10% ethyl acetate in heptane)