HuagongsheHuagongshe Chemistry Print Report · For research reference only
1-Methylimidazole → 3-Chloro-N-{2-cyano-6-methyl-3-[3-(methyloxy)phenyl]thieno[2,3-b]pyridin-4-yl}-benzenesulfonamide
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | 1-Methylimidazole | HCID 1390 | — |
| Reactant | N-{2-Bromo-6-methyl-3-[3-(methyloxy)phenyl]thieno[2,3-b]pyridin-4-yl}-3-chlorobenzenesulfonamide | HCID 53250396 | — |
| Catalyst | Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI) | HCID 24350 | — |
| Catalyst | HCID 178511492 | HCID 178511492 | — |
| Product | 3-Chloro-N-{2-cyano-6-methyl-3-[3-(methyloxy)phenyl]thieno[2,3-b]pyridin-4-yl}-benzenesulfonamide | HCID 68324072 | 31.5% |
Reaction Steps
A mixture of N-{2-bromo-6-methyl-3-[3-(methyloxy)phenyl]thieno[2,3-b]pyridin-4-yl}-3-chlorobenzenesulfonamide (85 mg, 0.162 mmol) (Example 33), potassium ferrocyanide (13.71 mg, 0.032 mmol), copper(I) iodide (3.09 mg, 0.016 mmol) in 1-methylimidazole (1 mL, 12.55 mmol) was subjected to microwave reaction at 160° C. for 1 h. Purification by chromatography on silica gel, eluting with a gradient of 40-60% ethyl acetate in cyclohexane, afforded the title compound (24 mg). LCMS (A) m/z: 470 [M+1]+, Rt 1.58 min (acidic), Rt 1.09 min (basic).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09029545B2 |
| Source dataset | uspto-grants-2015_05 |
| ORD ID | ord-56f80372eee3410eaea15a3f5da8e19d |
| Source note | uspto-grants-2015_05 |