Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Potassium Iodide | HCID 4875 | — |
| Reactant | Potassium Carbonate | HCID 11430 | — |
| Reactant | Pyrrolidine | HCID 31268 | — |
| Reactant | HCID 57625497 | HCID 57625497 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | HCID 57625531 | HCID 57625531 | 102.6% |
Reaction Steps
To a solution of 5-bromo-1-(3-chloropropyl)-1H-indazole (2.14 g, 7.84 mmol) in DMF (40 mL) was added potassium iodide (1.3 mg, 7.8 mmol) and K2CO3 (5.40 g, 39.2 mmol) under N2 (g). Then pyrrolidine (17.2 ml, 26.6 mmol) was added. The reaction was heated to 50° C. for 20 h. The reaction was diluted with EtOAc (100 mL) and washed with a 5% LiCl solution (4×). The organics were dried (Na2SO4), filtered, and concentrated to give the title compound (2.48 g, quant.) as a brown oil: 1H NMR (300 MHz, CDCl3) δ 7.93 (s, 1H), 7.85 (d, J=1.2 Hz, 1H), 7.45-7.41 (dd, J=8.9, 1.7 Hz, 1H), 7.36 (d, J=8.9 Hz, 1H), 4.45 (t, J=6.7 Hz, 1H), 2.44-2.36 (m, 6H), 2.15-2.07 (m, 2H), 1.78-1.74 (m, 4H); ESI MS m/z 308 [M+H]+.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08273770B2 |
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| Source dataset | uspto-grants-2012_09 |
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| ORD ID | ord-fa592954582845cd83aa1a9d4cc5c507 |
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| Source note | uspto-grants-2012_09 |
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