Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Nitrogen | HCID 947 | — |
| Reactant | Dichloromethane | HCID 6344 | — |
| Reactant | 2-Formylphenylboronic acid | HCID 292189 | — |
| Reactant | HCID 67011693 | HCID 67011693 | — |
| Catalyst | Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+) | HCID 178418228 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Solvent | Sodium Carbonate | HCID 10340 | — |
| Product | HCID 11180883 | HCID 11180883 | 74.4% |
Reaction Steps
A solution of N-[2-((3S)-3-[4-(5-bromopyridin-2-yl)-4-hydroxycyclohexyl]aminopyrrolidin-1-yl)-2-oxoethyl]-3-(trifluoromethyl)benzamide (30.0 mg, 0.0527 mmol) and (2-formylphenyl)boronic acid (8.6 mg, 0.052 mmol) in DMF (0.60 mL) and aqueous sodium carbonate (2M, 0.198 mL) was degassed with N2 for 5 minutes. Then [1,1′-bis(diphenylphosphino)ferrocene]-dichloropalladium(II), complex with dichloromethane (1:1) (2.2 mg, 0.0026 mmol) was added in under N2 flush. The reaction mixture was degassed with N2 for another 5 minutes and then the tube was sealed. The reaction mixture was heated under microwave at 130° C. for 5 minutes. After cooling down, the reaction mixture was filtered through a short pad of silica gel and washed with CH3CN. The resulting solution was acidified with TFA to pH 1˜2, then was subjected to purification on Prep-HPLC. The appropriate fractions were lypholized to give the product (23 mg, 53%) as a white powder. MS: (M+H)+ 595.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US08697870B2 |
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| Source dataset | uspto-grants-2014_04 |
|---|
| ORD ID | ord-5661bc6feaa749bba0dc2f49236160de |
|---|
| Source note | uspto-grants-2014_04 |
|---|
