HuagongsheHuagongshe Chemistry Print Report · For research reference only
Sodium Carbonate → 5-[4-(4-methoxypyridin-3-yl)benzyl]-7,8-dihydro-5H-[1,3]dioxolo[4,5-g]isoquinoline-6-carboxylic acid tert-butyl ester
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Sodium Carbonate | HCID 10340 | — |
| Reactant | Triphenylphosphine | HCID 11776 | — |
| Reactant | 4-Methoxypyridine-3-boronic acid | HCID 2762556 | — |
| Reactant | 5-(4-Bromobenzyl)-7,8-dihydro-5H-[1,3]dioxolo[4,5-g]isoquinoline-6-carboxylic acid tert-butyl ester | HCID 59744265 | — |
| Reactant | 5-[4-(4-Methoxypyridin-3-yl)benzyl]-5,6,7,8-tetrahydro-[1,3]dioxolo[4,5-g]isoquinoline dihydrochloride salt | HCID 69081323 | — |
| Catalyst | palladium(II) acetate | HCID 167845 | — |
| Solvent | Isopropanol | HCID 3776 | — |
| Product | 5-[4-(4-methoxypyridin-3-yl)benzyl]-7,8-dihydro-5H-[1,3]dioxolo[4,5-g]isoquinoline-6-carboxylic acid tert-butyl ester | HCID 59744288 | — |
Reaction Steps
The synthesis of 5-[4-(4-methoxypyridin-3-yl)benzyl]-5,6,7,8-tetrahydro-[1,3]dioxolo[4,5-g]isoquinoline dihydrochloride salt 45 is shown in Scheme-12. Reaction of compound 38 with 4-methoxypyridine-3-boronic acid 19 in the presence of Palladium (II) acetate, triphenylphosphine, and Na2CO3 in anhydrous 2-propanol yielded 5-[4-(4-methoxypyridin-3-yl)benzyl]-7,8-dihydro-5H-[1,3]dioxolo[4,5-g]isoquinoline-6-carboxylic acid tert-butyl ester 43 which was treated with trifluoroacetic acid in dichloromethane to get 5-[4-(4-methoxypyridin-3-yl)benzyl]-5,6,7,8-tetrahydro-[1,3]dioxolo[4,5-g]isoquinoline trifluoro acetate salt 44. Compound 44 was treated by 37% HCl, 1N NaOH followed by 2M HCl/Ether in MeOH-Ether to obtain 45.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08507523B2 |
| Source dataset | uspto-grants-2013_08 |
| ORD ID | ord-efa10c3d971f4af58a9df489c86e31ce |
| Source note | uspto-grants-2013_08 |