HuagongsheHuagongshe Chemistry Print Report · For research reference only
Dimethylformamide → 3-[4-(1-carbomethoxy-1-cyclohexyl)methoxyphenyl]methyl-7-methyl-2-propyl-3H-imidazo[4,5-b]pyridine
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Dimethylformamide | HCID 6228 | — |
| Reactant | 18-Crown-6 | HCID 28557 | — |
| Reactant | Methyl 2-bromo-2-cyclohexylacetate | HCID 295968 | — |
| Reactant | 3-(4-hydroxyphenyl)methyl-7-methyl-2-propyl-3H-imidazo[4,5-b]pyridine | HCID 19385643 | — |
| Product | 3-[4-(1-carbomethoxy-1-cyclohexyl)methoxyphenyl]methyl-7-methyl-2-propyl-3H-imidazo[4,5-b]pyridine | HCID 19385656 | 10% |
Reaction Steps
A solution of 0.200 g (0.71 mmol) of 3-(4-hydroxyphenyl)methyl-7-methyl-2-propyl-3H-imidazo[4,5-b]pyridine (Step D, Example 2) dissolved in 0.5 mL of DMF was deprotonated (82 mg KH, 0.188 g 18-crown-6) and alkylated with 0.184 g (0.78 mmol) of commercially available methyl 2-bromo-2-cyclohexylacetate similarly to the procedure described in Example 2, Step E. Purification on a silica gel flash chromatography column eluted with 30% ethyl acetate/hexane afforded 0.029 g (10%) of the title compound.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US05240938 |
| Source dataset | uspto-grants-1993_08 |
| ORD ID | ord-b817ea8df2cb43aea52f1071ac476495 |
| Source note | uspto-grants-1993_08 |