Ethyl orthoformate → HCID 178505977、化合物
反応式
[F:1][C:2]1[CH:3]=[C:4]([NH2:9])[C:5]([NH2:8])=[N:6][CH:7]=1.[CH2:10](OC(OCC)OCC)C>C(O)=O>[F:1][C:2]1[CH:3]=[C:4]2[N:9]=[CH:10][NH:8][C:5]2=[N:6][CH:7]=1参加物
4
反応条件
- 温度
- 100 °C
実験手順
A stirred mixture of 5-fluoropyridine-2,3-diamine (1.13 g) from Step 1 of this Example, formic acid (0.5 mL), and triethylorthoformate (15 mL) was heated at 100° C. for 1 h. The reaction mixture was cooled to rt, filtered, and the filtrate was concentrated under reduced pressure. The residue was purified via silica gel flash chromatography eluting with 100% DCM to 10% MeOH in DCM to afford 6-fluoro-3H-imidazo[4,5-b]pyridine (760 mg, 36% over two steps) as a yellow solid. 1H NMR (500 MHz, DMSO-d6) δ 13.09 (br s, 1H), 8.49 (s, 1H), 8.37 (s, 1H), 7.97 (d, J=7.9 Hz, 1H). LCMS (ESI) m/z 138 (M+H)+.
後処理
- temperatureThe reaction mixture was cooled to rt
- filtrationfiltered
- concentrationthe filtrate was concentrated under reduced pressure
- customThe residue was purified via silica gel flash chromatography
- washeluting with 100% DCM to 10% MeOH in DCM
出典と根拠
- ORDレコード
- ord-4e4c39ae4afa4606a0f9cfe389f6d4bf
- 出典データセット
- uspto-grants-2015_02
- 特許番号
- US08952058B2
反応ノート
読み込み中…