関与物質
| 役割 | 名称 | HCID | 仕込み量 |
|---|
| 反応物 | Water | HCID 962 | — |
| 反応物 | Dimethylformamide | HCID 6228 | — |
| 反応物 | Ammonium Hydroxide | HCID 14923 | — |
| 反応物 | Ammonium Chloride | HCID 25517 | — |
| 反応物 | 4-Iodo-1H-pyrrolo[2,3-b]pyridine | HCID 21877415 | — |
| 触媒 | Zinc cyanide (Zn(CN)2) | HCID 11186 | — |
| 触媒 | Ferrocene-1,1'-bis-(diphenylphosphine) | HCID 635956 | — |
| 触媒 | Bis(dibenzylideneacetone)palladium | HCID 9811564 | — |
| 生成物 | 1H-pyrrolo(2,3-b)pyridine-4-carbonitrile | HCID 11715196 | 74% |
反応手順
To a solution of (4.7 g, 19.3 mmol) of 4-Iodo-1H-pyrrolo[2,3-b]pyridine in degassed DMF (25 mL) was added Pd2(dba)3 (10 mg), dppf (15 mg), degassed H2O (2 mL) and Zn(CN)2 (1.4 g, 11.6 mmol). The mixture was stirred at 90° C. under nitrogen for 20 hr, then cooled to 70° C. and 75 mL of a 4:1:4 mixture of saturated NH4Cl:NH4OH:H2O was added. The mixture was stirred at 5° C. for 20 min. and the resulting precipitate filtered off, washed with 75 mL 4:1:5 mixture of saturated NH4Cl:NH4OH:H2O, 500 mL H2O and 100 mL toluene, then dried in vacuo to give 2.06 g (74%) 1H-Pyrrolo[2,3-b]pyridine-4-carbonitrile. MS (ES+): 143 [MH+]. 1H NMR (DMSO-d6, 400 MHz): δ 6.65 (d, 1H, J=3.2), 7.56 (d, 1H, J=4.8 Hz), 7.84 (d, 1H, J=4.0 Hz), 8.40 (d, 1H, J=4.8 Hz).
情報源と証拠
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| 特許番号 | US06949563B2 |
|---|
| 出典データセット | uspto-grants-2005_09 |
|---|
| ORD ID | ord-168a8ade12a14fb9981eb872fe0c2ad9 |
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| 出典メモ | uspto-grants-2005_09 |
|---|
