HuagongsheHuagongshe Chemistry Print Report · For research reference only
Methyl 4-(bromomethyl)-3-methoxybenzoate → 4-[5-(Cyclopentyloxycarbonyl)amino-1-methylindazol-3-ylmethyl]-3-methoxybenzoic acid
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Methyl 4-(bromomethyl)-3-methoxybenzoate | HCID 2759828 | — |
| Reactant | Methyl 4-[5-(cyclopentyloxycarbonyl)amino-1-methylindazol-3-ylmethyl]-3-methoxybenzoate | HCID 14626827 | — |
| Reactant | 3-Bromo-5-(cyclopentyloxycarbonyl)amino-1-methylindazole | HCID 23365904 | — |
| Catalyst | Zinc | HCID 23994 | — |
| Catalyst | Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+) | HCID 178418228 | — |
| Product | 4-[5-(Cyclopentyloxycarbonyl)amino-1-methylindazol-3-ylmethyl]-3-methoxybenzoic acid | HCID 14626829 | — |
Reaction Steps
The process may be carried out, for example, using a stoichiometric amount of activated zinc dust and a catalytic quantity of a transition metal catalyst, such as, for example, dichloro[1,1'-bis(diphenylphosphino)ferrocene]palladium (II) or dichlorobis(triphenylphosphine)nickel (II) to couple, for example, 3-bromo-5-(cyclopentyloxycarbonyl)amino-1-methylindazole with, for example, methyl 4-bromomethyl-3-methoxybenzoate to afford methyl 4-[5-(cyclopentyloxycarbonyl)amino-1-methylindazol-3-ylmethyl]-3-methoxybenzoate; followed by decomposition of the ester to afford 4-[5-(cyclopentyloxycarbonyl)amino-1-methylindazol-3-ylmethyl]-3-methoxybenzoic acid.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US05338734 |
| Source dataset | uspto-grants-1994_08 |
| ORD ID | ord-77d6f3d134844fd885229a447ce5059e |
| Source note | uspto-grants-1994_08 |