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3,6-Dichloropyridazine → 6-((9-cyclopentyl-9H-pyrido[4',3':4,5]pyrrolo[2,3-d]pyrimidin-2-yl)amino)-3-chloro-pyridazine
関与物質
| 役割 | 名称 | HCID | 仕込み量 |
|---|---|---|---|
| 反応物 | 3,6-Dichloropyridazine | HCID 67331 | — |
| 反応物 | 1,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine) | HCID 636044 | — |
| 反応物 | Sodium t-butoxide | HCID 23676156 | — |
| 反応物 | 9-Cyclopentyl-9H-pyrido[4',3':4,5]pyrrolo[2,3-d]pyrimidin-2-amine | HCID 58299585 | — |
| 触媒 | (1E,4E)-1,5-diphenylpenta-1,4-dien-3-one; palladium | HCID 6505921 | — |
| 溶媒 | Toluene | HCID 1140 | — |
| 生成物 | 6-((9-cyclopentyl-9H-pyrido[4',3':4,5]pyrrolo[2,3-d]pyrimidin-2-yl)amino)-3-chloro-pyridazine | HCID 58299683 | 97% |
反応条件
| 温度 | 100 °C |
|---|
反応手順
A mixture of compound 4 (1.50 g, 5.92 mmol), 3,6-dichloropyridazine (0.882 g, 5.92 mmol), bis(dibenzylideneacetone)palladium (0.170 g, 0.296 mmol), Xantphos (0.514 g, 0.888 mmol) and sodium tert-butoxide (0.854, 8.88 mmol) in toluene (80 mL) was purged with nitrogen. The reaction was then heated at 100° C. for one hour in a sealed vessel. After cooling to room temperature, the mixture was loaded onto a silica gel column and eluted with 2-10% methanol/DCM. Evaporation of combined fractions provided compound 140 (2.1 g) as a yellowish solid. LCMS-ESI, M+1: 366.1
情報源と証拠
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| 特許番号 | US08841312B2 |
| 出典データセット | uspto-grants-2014_09 |
| ORD ID | ord-99dcd0086e284629ac36e9e5d3bd5370 |
| 出典メモ | uspto-grants-2014_09 |