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Phenylsilane → 5-Phenyl-3-(tetrahydro-thiopyran-4-ylamino)-thiophene-2-carboxylic acid methyl ester
関与物質
| 役割 | 名称 | HCID | 仕込み量 |
|---|---|---|---|
| 反応物 | Phenylsilane | HCID 12752 | — |
| 反応物 | Tetrahydrothiopyran-4-one | HCID 66173 | — |
| 反応物 | Methyl 3-amino-5-phenylthiophene-2-carboxylate | HCID 700562 | — |
| 触媒 | Dibutyltin dichloride | HCID 12688 | — |
| 溶媒 | Tetrahydrofuran | HCID 8028 | — |
| 生成物 | 5-Phenyl-3-(tetrahydro-thiopyran-4-ylamino)-thiophene-2-carboxylic acid methyl ester | HCID 59752374 | 56.5% |
反応手順
Reductive amination of 3-amino-5-phenyl-thiophene-2-carboxylic acid methyl ester (0.933 g, 4.0 mmol) and tetrahydro-thiopyran-4-one (0.464 g, 4.0 mmol) in THF (1.0 mL) employing Bu2SnCl2 (60.5 mg, 0.2 mmol) and PhSiH3 (0.476 g, 0.542 mL) was carried out as described for example 13, step 1 gave 5-phenyl-3-(tetrahydro-thiopyran-4-ylamino)-thiophene-2-carboxylic acid methyl ester (0.753 g, 56.3%). NMR 1H (CDCl3, 400 MHz): 7.64-7.6 (m, 2H), 7.44-7.34 (m, 3H), 6.9 (brm, 1H), 6.81 (brs, 1H), 3.84 (s, 3H), 3.5-3.4 (m, 1H), 2.85-2.7 (m, 4H), 2.4-2.25 (m, 2H), 1.85-1.7 (m, 2H).
情報源と証拠
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| 特許番号 | US08829030B2 |
| 出典データセット | uspto-grants-2014_09 |
| ORD ID | ord-9887b9a5d4de4344accb803ab0a9f125 |
| 出典メモ | uspto-grants-2014_09 |