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Chlorosulfonyl isocyanate → 6-methoxy-2-methyl-1H-indole-3-carbonitrile
関与物質
| 役割 | 名称 | HCID | 仕込み量 |
|---|---|---|---|
| 反応物 | Chlorosulfonyl isocyanate | HCID 70918 | — |
| 反応物 | Sodium Bicarbonate | HCID 516892 | — |
| 反応物 | 6-methoxy-2-methyl-1H-indole | HCID 10844709 | — |
| 溶媒 | Dimethylformamide | HCID 6228 | — |
| 溶媒 | Acetonitrile | HCID 6342 | — |
| 生成物 | 6-methoxy-2-methyl-1H-indole-3-carbonitrile | HCID 13904640 | 81% |
反応手順
To a solution of 6-methoxy-2-methyl-1H-indole (3.9 g, 24 mmol) in acetonitrile (200 mL) and DMF (20 mL) is added dropwise a solution of ClSO2NCO (4 mL, 1.3 eq.) in acetonitrile (31 mL) at 0° C. After the addition, the mixture is stirred at room temperature for 3 h. Then it is poured into ice water and saturated NaHCO3 is added to it until it becomes basic. The aqueous phase is extracted with CH2Cl2 and then evaporated. The residue is purified with flash column chromatography on silica gel using EtOAc/petroleum ether (1/5) as eluent to yield 81% of 6-methoxy-2-methyl-1H-indole-3-carbonitrile.
情報源と証拠
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| 特許番号 | US07868037B2 |
| 出典データセット | uspto-grants-2011_01 |
| ORD ID | ord-a3b2adcd5e7a4039b8a70e9d60a9474a |
| 出典メモ | uspto-grants-2011_01 |