HuagongsheHuagongshe Chemistry Print Report · For research reference only
Methyl iodide → (S)-ethyl 2-tert-butoxy-2-(7-(4-chlorophenyl)-2-(1,2-dimethyl-1H-pyrrolo[2,3-b]pyridin-5-yl)-5-methylbenzo[d]thiazol-6-yl)acetate
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Methyl iodide | HCID 6328 | — |
| Reactant | Cesium carbonate | HCID 10796 | — |
| Reactant | (S)-ethyl 2-tert-butoxy-2-(7-(4-chlorophenyl)-5-methyl-2-(2-methyl-1H-pyrrolo[2,3-b]pyridin-5-yl)benzo[d]thiazol-6-yl)acetate | HCID 86700195 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | (S)-ethyl 2-tert-butoxy-2-(7-(4-chlorophenyl)-2-(1,2-dimethyl-1H-pyrrolo[2,3-b]pyridin-5-yl)-5-methylbenzo[d]thiazol-6-yl)acetate | HCID 86700196 | — |
Reaction Steps
To a solution of (S)-ethyl 2-tert-butoxy-2-(7-(4-chlorophenyl)-5-methyl-2-(2-methyl-1H-pyrrolo[2,3-b]pyridin-5-yl)benzo[d]thiazol-6-yl)acetate (70 mg, 0.128 mmol) in DMF (5 mL) was added cesium carbonate (54 mg, 0.166 mmol). The reaction solution was stirred at room temperature for 5 minutes, then iodomethane (24 mg, 0.166 mmol) was added. The reaction solution was stirred for 30 minutes and quenched with water. Volatiles were removed and the residue partitioned between ethyl acetate and water. The organic phase was washed with brine, dried (MgSO4) and concentrated to give crude which was purified by chromatographic column to afford the desired product. LCMS-ESI+: calc'd for C31H32 ClN3O3S: 562.3 (M+H+); Found: 562.3 (M+H+).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08987250B2 |
| Source dataset | uspto-grants-2015_03 |
| ORD ID | ord-0bfa5909db674dccb69e5dfee858d057 |
| Source note | uspto-grants-2015_03 |