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6-Azaindole → tert-Butyl 4-{1H-pyrrolo[2,3-c]pyridin-3-yl}-1,2,3,6-tetrahydropyridine-1-carboxylate
関与物質
| 役割 | 名称 | HCID | 仕込み量 |
|---|---|---|---|
| 反応物 | 6-Azaindole | HCID 9219 | — |
| 反応物 | Potassium Hydroxide | HCID 14797 | — |
| 反応物 | tert-Butyl 4-oxopiperidine-1-carboxylate | HCID 735900 | — |
| 溶媒 | Methanol | HCID 887 | — |
| 生成物 | tert-Butyl 4-{1H-pyrrolo[2,3-c]pyridin-3-yl}-1,2,3,6-tetrahydropyridine-1-carboxylate | HCID 59559369 | 92% |
反応手順
A suspension of 1H-pyrrolo[2,3-c]pyridine (0.95 g, 8.05 mmol), tert-butyl 4-oxo-piperidine-1-carboxylate (1.70 g, 8.54 mmol) and KOH (0.95 g, 17.0 mmol) in MeOH (10 mL) was heated at reflux overnight. The mixture was added to ice-water (50 mL) and then MeOH (50 mL) was added. The resulting solution was concentrated to circa 50 mL and then extracted three times with DCM/MeOH (9:1, 50 mL). The organic layers were combined and concentrated and the residue was purified by flash chromatography (9:1 DCM/MeOH) to yield the title compound as a light yellow solid (2.21 g, 92%). MS (ESI+) m/z=300 (M+H)+.
情報源と証拠
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| 特許番号 | US09227967B2 |
| 出典データセット | uspto-grants-2016_01 |
| ORD ID | ord-ef0c13e8c0354ee09168905c946e3d4d |
| 出典メモ | uspto-grants-2016_01 |