3-(4-bromophenyl)-N-methylpropan-1-amine

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

Procedure: Using a procedure analogous to that used to prepare 22B, 23A (1.6 g, 7.0 mmol) was reduced with borane in THF to yield 23B (1.45 g, 97%) as a clear oil. MS (ESI) m/z 214.22/216.22 (M+H)+.

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

Procedure: Using a procedure analogous to that used to prepare 22B, 23A (1.6 g, 7.0 mmol) was reduced with borane in THF to yield 23B (1.45 g, 97%) as a clear oil. MS (ESI) m/z 214.22/216.22 (M+H)+.

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

Procedure: 3-Isocyanatobenzonitrile (202 mg, 1.4 mmol) was added in one portion to a solution of 22B (320 mg, 1.4 mmol) in methylene chloride (10 mL). After stirring overnight the reaction mixture was concentrated in vacuo and purified by flash chromatography (0 to 100% EtOAc in hexanes) to yield 22C (430 mg, 88%) as a clear oil. MS (ESI) m/z 371.92/373.92 (M+H)+. was concentrated in vacuo purified by flash chromatography (0 to 100% EtOAc in hexanes)

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Borane in THF (1.0 M, 28 mL, 28 mmol) was added dropwise to a solution of 22A (1.6 g, 7.0 mmol) in THF (17.5 mL). After stirring the reaction mixture for 30 min at 0° C. the mixture was refluxed for 4 h. Methanol (20 mL) was added to the mixture at 0° C. followed by the addition of 20 mL 6.0 M HCl dropwise. After refluxing for 30 min the volatiles were removed in vacuo. 50% NaOH (12 mL) was added dropwise while maintaining the temperature below 30° C. The resulting mixture was diluted with water (100 mL) and extracted with diethyl ether (3×100 mL). The organics were combined, washed with brine, dried over Na2SO4 and concentrated in vacuo to yield 22B (1.57 g, 97%) as a clear oil. MS (ESI) m/z 227.99/229.99 (M+H)+. was refluxed for 4 h After refluxing for 30 min the volatiles were removed in vacuo 50% NaOH (12 mL) was added dropwise while maintaining the temperature below 30° C The resulting mixture was diluted with water (100 mL) extracted with diethyl ether (3×100 mL) washed with brine dried over Na2SO4 concentrated in vacuo

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Borane in THF (1.0 M, 28 mL, 28 mmol) was added dropwise to a solution of 22A (1.6 g, 7.0 mmol) in THF (17.5 mL). After stirring the reaction mixture for 30 min at 0° C. the mixture was refluxed for 4 h. Methanol (20 mL) was added to the mixture at 0° C. followed by the addition of 20 mL 6.0 M HCl dropwise. After refluxing for 30 min the volatiles were removed in vacuo. 50% NaOH (12 mL) was added dropwise while maintaining the temperature below 30° C. The resulting mixture was diluted with water (100 mL) and extracted with diethyl ether (3×100 mL). The organics were combined, washed with brine, dried over Na2SO4 and concentrated in vacuo to yield 22B (1.57 g, 97%) as a clear oil. MS (ESI) m/z 227.99/229.99 (M+H)+. was refluxed for 4 h After refluxing for 30 min the volatiles were removed in vacuo 50% NaOH (12 mL) was added dropwise while maintaining the temperature below 30° C The resulting mixture was diluted with water (100 mL) extracted with diethyl ether (3×100 mL) washed with brine dried over Na2SO4 concentrated in vacuo

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

Procedure: Using a procedure analogous to that used to prepare 22B, 23A (1.6 g, 7.0 mmol) was reduced with borane in THF to yield 23B (1.45 g, 97%) as a clear oil. MS (ESI) m/z 214.22/216.22 (M+H)+.

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

Procedure: 3-Isocyanatobenzonitrile (202 mg, 1.4 mmol) was added in one portion to a solution of 22B (320 mg, 1.4 mmol) in methylene chloride (10 mL). After stirring overnight the reaction mixture was concentrated in vacuo and purified by flash chromatography (0 to 100% EtOAc in hexanes) to yield 22C (430 mg, 88%) as a clear oil. MS (ESI) m/z 371.92/373.92 (M+H)+. was concentrated in vacuo purified by flash chromatography (0 to 100% EtOAc in hexanes)

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Borane in THF (1.0 M, 28 mL, 28 mmol) was added dropwise to a solution of 22A (1.6 g, 7.0 mmol) in THF (17.5 mL). After stirring the reaction mixture for 30 min at 0° C. the mixture was refluxed for 4 h. Methanol (20 mL) was added to the mixture at 0° C. followed by the addition of 20 mL 6.0 M HCl dropwise. After refluxing for 30 min the volatiles were removed in vacuo. 50% NaOH (12 mL) was added dropwise while maintaining the temperature below 30° C. The resulting mixture was diluted with water (100 mL) and extracted with diethyl ether (3×100 mL). The organics were combined, washed with brine, dried over Na2SO4 and concentrated in vacuo to yield 22B (1.57 g, 97%) as a clear oil. MS (ESI) m/z 227.99/229.99 (M+H)+. was refluxed for 4 h After refluxing for 30 min the volatiles were removed in vacuo 50% NaOH (12 mL) was added dropwise while maintaining the temperature below 30° C The resulting mixture was diluted with water (100 mL) extracted with diethyl ether (3×100 mL) washed with brine dried over Na2SO4 concentrated in vacuo