Binap, (A+-)- → 4-chloro-6-(3-isopropoxy-benzylamino)-2H-phthalazin-1-one

関与物質

役割	名称	HCID	仕込み量
反応物	Binap, (A+-)-	HCID 634876	—
反応物	1-(3-Isopropoxyphenyl)methanamine	HCID 2760935	—
反応物	Sodium t-butoxide	HCID 23676156	—
反応物	6-Bromo-4-chlorophthalazin-1(2H)-one	HCID 53308487	—
触媒	Bis(dibenzylideneacetone)palladium	HCID 9811564	—
溶媒	Ethyl Acetate	HCID 8857	—
溶媒	Dimethylacetamide	HCID 31374	—
生成物	4-chloro-6-(3-isopropoxy-benzylamino)-2H-phthalazin-1-one	HCID 24948345	21.8%

反応手順

A mixture 6-bromo-4-chloro-2H-phthalazin-1-one (156 mg, 0.601 mmol), 1-(3-isopropoxyphenyl)methanamine (116 mg, 0.702 mmol), Pd2(dba)3 (53 mg, 0.0578 mmol), rac-BINAP (113 mg, 0.181 mmol) and NaOtBu (139 mg, 1.445 mmol) in DMA (6 mL) was heated at 85° C. for 2 h. The mixture was allowed to cool, diluted with EtOAc and washed with water. The organic layer was washed with sat.aq. NaHCO3, brine and dried (Na2SO4). Chromatography on silica (EtOAc/hexanes) afforded 4-chloro-6-(3-isopropoxy-benzylamino)-2H-phthalazin-1-one (45 mg) as an off white solid, 1H (400 MHz, d6-DMSO) δ: 1.22 (d, 6H), 4.40 (d, 2H), 4.57 (quintet, 1H), 6.80 (m, 2H), 6.91 (m, 2H), 7.16 (dd, 1H), 7.22 (t, 1H), 7.64 (t, 1H), 7.92 (d, 1H), 12.34 (s, 1H) ppm; m/z (M+1) 344.01.

情報源と証拠

DOI	10.6084/m9.figshare.5104873.v1
特許番号	US08349836B2
出典データセット	uspto-grants-2013_01
ORD ID	ord-16682b0598ad4ef38a7b5359d0c89495
出典メモ	uspto-grants-2013_01