Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Water | HCID 962 | — |
| Reactant | 4-Toluenesulfonyl chloride | HCID 7397 | — |
| Reactant | Sodium hydride | HCID 24758 | — |
| Reactant | HCID 67959733 | HCID 67959733 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | HCID 67959813 | HCID 67959813 | 99% |
Reaction Steps
NaH (60% in mineral oil) (34 mg, 0.85 mmol) was added to a solution of 5-(6-cyclopropylpyrazin-2-yl)-3-iodo-1H-indole (280 mg, 0.78 mmol) in THF (4 mL) at 0° C. The mixture was stirred for 10 min at 0° C. and p-toluenesulfonyl chloride (163 mg, 0.85 mmol) was added and the mixture was warmed to RT. After 1 h, water was added and the mixture was extracted with EtOAc (3×). The combined organic layers were dried over anhydrous Na2SO4, filtered and concentrated to afford 5-(6-cyclopropylpyrazin-2-yl)-3-iodo-1-tosyl-1H-indole (394 mg, 0.76 mmol, 99% yield) as a yellow solid. MS (ESI, pos. ion) m/z: 516.0 (M+1).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US09090593B2 |
|---|
| Source dataset | uspto-grants-2015_07 |
|---|
| ORD ID | ord-61cee6607abe46e3a176bb9da11eeda3 |
|---|
| Source note | uspto-grants-2015_07 |
|---|