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Dimethylformamide → 7-Methyl-6-(pyridin-3-yl) imidazo[1,2-a]pyridine-3-carbaldehyde
関与物質
| 役割 | 名称 | HCID | 仕込み量 |
|---|---|---|---|
| 反応物 | Dimethylformamide | HCID 6228 | — |
| 反応物 | Sodium Carbonate | HCID 10340 | — |
| 反応物 | 3-Pyridinylboronic acid | HCID 2734378 | — |
| 反応物 | 6-Bromo-7-methylimidazo[1,2-a]pyridine-3-carbaldehyde | HCID 46739170 | — |
| 溶媒 | Ethyl Acetate | HCID 8857 | — |
| 生成物 | 7-Methyl-6-(pyridin-3-yl) imidazo[1,2-a]pyridine-3-carbaldehyde | HCID 86670596 | 62% |
反応手順
6-bromo-7-methylimidazo[1,2-a]pyridine-3-carbaldehyde (Compound of step 1, 2000 mg, 7.90 mmol), Pyridine-3-boronic acid (1170 mg, 9.49 mmol), dichlorobis (triphenylphosphine) palladium (II) (200 mg, 10% mmol) and 2M aqueous Na2CO3 (7 mL) were added to DMF (25 mL) and refluxed for 2 hours. The reaction mixture was diluted with ethyl acetate and washed with H2O and brine. The solvent was evaporated to obtain crude product, which was purified by column chromatography (silica gel, 1% methanol in chloroform) to obtain the title compound. Yield: 62%; 1H NMR (DMSO-d6; 300 MHz): δ 9.92 (s, 1H), 9.20 (s, 1H), 8.69-8.70 (m, 2H), 8.54 (s, 1H), 7.95-7.99 (m, 1H), 7.90 (s, 1H), 7.53-7.58 (m, 1H), 2.34 (s, 3H); MS: m/z 238 (M+1)+
情報源と証拠
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| 特許番号 | US08741932B2 |
| 出典データセット | uspto-grants-2014_06 |
| ORD ID | ord-f793354b8d7045b88172a688a1b6cc8d |
| 出典メモ | uspto-grants-2014_06 |