Benzenemethanamine, 3,5-dichloro- → 4-chloro-6-(3,5-dichloro-benzylamino)-2H-phthalazin-1-one

関与物質

役割	名称	HCID	仕込み量
反応物	Benzenemethanamine, 3,5-dichloro-	HCID 457602	—
反応物	Binap, (A+-)-	HCID 634876	—
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-(3,5-dichloro-benzylamino)-2H-phthalazin-1-one	HCID 24948534	2.3%

反応手順

A mixture 6-bromo-4-chloro-2H-phthalazin-1-one (97 mg, 0.374 mmol), 3,5-dichlorobenzylamine (0.057 mL, 0.424 mmol), Pd2(dba)3 (29 mg, 0.032 mmol), rac-BINAP (70 mg, 0.112 mmol) and NaOtBu (104 mg, 1.08 mmol) in DMA (5 mL) was heated at 80° C. for 1.5 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-(3,5-dichloro-benzylamino)-2H-phthalazin-1-one (3 mg) as a white solid, 1H (400 MHz, CDCl3) δ: 4.40 (s, 2H), 6.84 (m, 1H), 6.99 (m, 1H), 7.22 (m, 3H), 8.14 (m, 1H), 10.80 (s, 1H) ppm; m/z (M+1) 353.83.

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-e5414037facb43e5aecd795d788d6366
出典メモ	uspto-grants-2013_01