(2-phenoxyphenyl)methanamine;hydrochloride

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

Procedure: A mixture 6-bromo-4-chloro-2H-phthalazin-1-one (150 mg, 0.58 mmol), 2-phenoxy-benzylamine hydrochloride (151 mg, 0.64 mmol), Pd2(dba)3 (53 mg, 0.058 mmol), rac-BINAP (132 mg, 0.17 mmol) and NaOt-Bu (200 mg, 2.1 mmol) in DMA (6 mL) was heated at 80° C. for 1 h. The mixture was allowed to cool, diluted with EtOAc (25 mL) and washed with water (25 mL). The organic layer was dried over anhydrous sodium sulfate and concentrated. Chromatography on silica (EtOAc/hexanes) yielded the title compound. 4-Chloro-6-(2-phenoxy-benzylamino)-2H-phthalazin-1-one: 81 mg (37.0%): m/z (M+H)=378. 1H-NMR (DMSO-d6) δ: 12.77 (s, 1H), 8.34 (d, 1H), 8.03 (m, 1H), 7.82 (m, 3H), 7.71 (m, 1H), 7.56 (m, 3H), 7.42 (m, 2H), 7.33 (dd, 1H), 7.20 (s, 1H), 4.84 (d, 2H). to cool washed with water (25 mL) The organic layer was dried over anhydrous sodium sulfate concentrated

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

Procedure: A mixture 6-bromo-4-chloro-2H-phthalazin-1-one (150 mg, 0.58 mmol), 2-phenoxy-benzylamine hydrochloride (151 mg, 0.64 mmol), Pd2(dba)3 (53 mg, 0.058 mmol), rac-BINAP (132 mg, 0.17 mmol) and NaOt-Bu (200 mg, 2.1 mmol) in DMA (6 mL) was heated at 80° C. for 1 h. The mixture was allowed to cool, diluted with EtOAc (25 mL) and washed with water (25 mL). The organic layer was dried over anhydrous sodium sulfate and concentrated. Chromatography on silica (EtOAc/hexanes) yielded the title compound. 4-Chloro-6-(2-phenoxy-benzylamino)-2H-phthalazin-1-one: 81 mg (37.0%): m/z (M+H)=378. 1H-NMR (DMSO-d6) δ: 12.77 (s, 1H), 8.34 (d, 1H), 8.03 (m, 1H), 7.82 (m, 3H), 7.71 (m, 1H), 7.56 (m, 3H), 7.42 (m, 2H), 7.33 (dd, 1H), 7.20 (s, 1H), 4.84 (d, 2H). to cool washed with water (25 mL) The organic layer was dried over anhydrous sodium sulfate concentrated