Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Ethyl Acetate | HCID 8857 | — |
| Reactant | Trimethylsilyl iodide | HCID 85247 | — |
| Reactant | Sodium Bicarbonate | HCID 516892 | — |
| Reactant | HCID 20636403 | HCID 20636403 | — |
| Solvent | Chloroform | HCID 6212 | — |
| Product | HCID 178515977 | HCID 178515977 | — |
Reaction Steps
Under exclusion of moisture, to 500 mg (1.76 mmol) of 1-chloro-4-[(6-methoxy-pyridin-3-yl)methyl]-isoquinoline (step 28.6) in 9 ml of chloroform, 488 μl (3.58 mmol) of Me3SiI are added. Then the mixture is stirred for 8 h at 60° C. Dilution of the mixture with EtOAc and NaHCO3-solution, stirring and filtration of the suspension yields 1-chloro-4-[(6-hydroxy-pyridin-3-yl)methyl]-isoquinoline, contaminated with 1-iodo-4-[(6-hydroxy-pyridin-3-yl)methyl]-isoquinoline; FAB-MS: (M+H)+=271chloride/363iodide; HPLC(gradient20-100) tRef=10.2chloride/10.8iodide. From the filtrate, more product can be obtained by extraction with EtOAc.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US07323474B2 |
|---|
| Source dataset | uspto-grants-2008_01 |
|---|
| ORD ID | ord-c38cbda72f854502aa22cea5156d5c17 |
|---|
| Source note | uspto-grants-2008_01 |
|---|
