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2,3-Dimethoxybenzylamine → 4-chloro-6-(2,3-dimethoxy-benzylamino)-2H-phthalazin-1-one
関与物質
| 役割 | 名称 | HCID | 仕込み量 |
|---|---|---|---|
| 反応物 | 2,3-Dimethoxybenzylamine | HCID 78106 | — |
| 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-(2,3-dimethoxy-benzylamino)-2H-phthalazin-1-one | HCID 24948341 | 18.5% |
反応手順
A mixture 6-bromo-4-chloro-2H-phthalazin-1-one (150 mg, 0.578 mmol), 2,3-dimethoxybenzylamine (0.094 mL, 0.636 mmol), Pd2(dba)3 (53 mg, 0.058 mmol), rac-BINAP (112 mg, 0.180 mmol) and NaOtBu (139 mg, 1.445 mmol) in DMA (5 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-(2,3-dimethoxy-benzylamino)-2H-phthalazin-1-one (37 mg) as an off white solid, 1H (400 MHz, d6-DMSO) δ: 3.79 (s, 3H), 3.80 (s, 3H), 4.40 (d, 2H), 6.83 (s, 1H), 6.88 (dd, 1H), 7.00 (m, 2H), 7.14 (dd, 1H), 7.53 (t, 1H), 7.91 (d, 1H), 12.33 (bs, 1H) ppm; m/z (M+1) 345.92.
情報源と証拠
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| 特許番号 | US08044041B2 |
| 出典データセット | uspto-grants-2011_10 |
| ORD ID | ord-c34b5272a35345b694d5c94ef0f74584 |
| 出典メモ | uspto-grants-2011_10 |