HuagongsheHuagongshe Chemistry Print Report · For research reference only
Dabco → tert-Butyl 4-((5-cyanobenzo[d]oxazol-2-yl)methyl)-5-methoxy-7-methyl-1H-indole-1-carboxylate
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Dabco | HCID 9237 | — |
| Reactant | 3-Amino-4-hydroxybenzonitrile | HCID 271258 | — |
| Reactant | tert-Butyl 4-(2,2-dibromovinyl)-5-methoxy-7-methyl-1H-indole-1-carboxylate | HCID 86701482 | — |
| Solvent | N-methyl-2-pyrrolidone | HCID 13387 | — |
| Product | tert-Butyl 4-((5-cyanobenzo[d]oxazol-2-yl)methyl)-5-methoxy-7-methyl-1H-indole-1-carboxylate | HCID 86701743 | — |
Reaction Steps
A solution of tert-butyl 4-(2,2-dibromovinyl)-5-methoxy-7-methyl-1H-indole-1-carboxylate (Example 20-A) (0.720 g, 1.617 mmol) and 3-amino-4-hydroxybenzonitrile (0.325 g, 2.426 mmol) and DABCO (0.544 g, 4.85 mmol) in NMP (1.62 ml) was stirred at 100° C. for 16 hrs. The reaction mixture was cooled and loaded onto silica gel to purify via FCC eluting with Heptane/AcOEt:100/0 to 0/100 to obtain the title compound. MS (ESI+) m/z 418.34 (M+H).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09056874B2 |
| Source dataset | uspto-grants-2015_06 |
| ORD ID | ord-dd5aef5fa38948db94189ec498604d37 |
| Source note | uspto-grants-2015_06 |