HuagongsheHuagongshe Chemistry Print Report · For research reference only
Hydrochloric Acid → 1-(2'-Acetylaminobiphenyl-4-ylmethyl)-6,7-dimethoxy-3,4-dihydro-1H-isoquinoline-2-carboxylic acid tert-butyl ester
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Hydrochloric Acid | HCID 313 | — |
| Reactant | Sodium Carbonate | HCID 10340 | — |
| Reactant | Triphenylphosphine | HCID 11776 | — |
| Reactant | 1-(4-Bromo-benzyl)-6,7-dimethoxy-3,4-dihydro-1H-isoquinoline-2-carboxylic acid tert-butyl ester | HCID 58906471 | — |
| Reactant | 1-(2'-Acetylaminobiphenyl-4-ylmethyl)-6,7-dimethoxy-3,4-dihydro-1H-isoquinoline-2-carboxylic acid tert-butyl ester | HCID 59744289 | — |
| Catalyst | palladium(II) acetate | HCID 167845 | — |
| Solvent | Diethyl Ether | HCID 3283 | — |
| Solvent | Isopropanol | HCID 3776 | — |
| Product | 1-(2'-Acetylaminobiphenyl-4-ylmethyl)-6,7-dimethoxy-3,4-dihydro-1H-isoquinoline-2-carboxylic acid tert-butyl ester | HCID 59744289 | — |
| Product | N-[4'-(6,7-dimethoxy-1,2,3,4-tetrahydro-isoquinolin-1-ylmethyl)-biphenyl-2-yl]acetamide hydrochloride salt | HCID 69270574 | — |
Reaction Steps
1-(2′-Acetylaminobiphenyl-4-ylmethyl)-6,7-dimethoxy-3,4-dihydro-1H-isoquinoline-2-carboxylic acid tert-butyl ester 17 was synthesized by the Suzuki coupling of 1-(4-bromobenzyl)-6,7-dimethoxy-3,4-dihydro-1H-isoquinoline-2-carboxylic acid tert-butyl ester 1 with 2-acethylaminophenylboronic acid 16 using Palladium(II) acetate, triphenylphosphine, and Na2CO3 in anhydrous isopropanol. Reaction of compound 17 with 2 M HCl solution in diethylether yielded N-[4′-(6,7-dimethoxy-1,2,3,4-tetrahydro-isoquinolin-1-ylmethyl)-biphenyl-2-yl]acetamide hydrochloride salt 18 (Scheme-5).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08507523B2 |
| Source dataset | uspto-grants-2013_08 |
| ORD ID | ord-7a3fb91fe2b74c82acd27e4e6cc16a0e |
| Source note | uspto-grants-2013_08 |