Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Water | HCID 962 | — |
| Reactant | Chloroacetone | HCID 6571 | — |
| Reactant | Cesium carbonate | HCID 10796 | — |
| Reactant | HCID 89543743 | HCID 89543743 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | HCID 89543798 | HCID 89543798 | 33.1% |
Reaction Steps
To a mixture of N-(2-methoxy-4-(7-oxo-4,5,6,7-tetrahydrobenzo[d]isoxazol-3-yl)phenyl)formamide (2.66 g, 9.28 mmol), Cs2CO3 (5.37 g, 27.9 mmol), and KI (308 mg, 1.86 mmol) in dry DMF (40 ml) was added chloroacetone (7.72 g, 18.57 mmol) dropwise. The reaction was stirred at 55° C. over night. Reaction mixture was worked up with water and DCM, organic phase was washed with water and brine, dried over sodium sulfate and concentrated. The product was purified by chromatography on silica gel using a mixture of ethyl acetate and hexanes as the eluent to furnish 1.05 g of the title compound, MS(M+H)+=343.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US09096582B2 |
|---|
| Source dataset | uspto-grants-2015_08 |
|---|
| ORD ID | ord-aa41e9541d1b48539f28a508596d661d |
|---|
| Source note | uspto-grants-2015_08 |
|---|