Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Dimethylformamide | HCID 6228 | — |
| Reactant | Dichloromethane | HCID 6344 | — |
| Reactant | Potassium Carbonate | HCID 11430 | — |
| Reactant | 5-Bromo-N-isopropylpicolinamide | HCID 26370111 | — |
| Reactant | HCID 67355913 | HCID 67355913 | — |
| Catalyst | Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+) | HCID 178418228 | — |
| Product | HCID 24759309 | HCID 24759309 | — |
Reaction Steps
To a solution of (4-{[(3R)-7-cyclohexyl-3-hydroxy-6-oxo-1,7-diazaspiro[4.4]non-1-yl]-methyl}-2-fluorophenyl)boronic acid (24.0 mg, 0.0000614 mol; which was prepared by using procedures that were analogous to those described for the synthesis of Example 32, steps 1-3 using peak 2 from step 2) and 5-bromo-N-isopropylpyridine-2-carboxamide (18 mg, 0.000074 mol) in DMF (0.8 mL, 0.01 mol) was added [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II), complex with DCM (1:1) (3.01 mg, 3.68E-6 mol) and potassium carbonate (25 mg, 0.00018 mol). The resulting mixture was heated at 130° C. under an atmosphere of nitrogen for 16 h to afford the desired product which was purified by prep-HPLC. LC/MS: 509.2 (M+1H)+.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US07998959B2 |
|---|
| Source dataset | uspto-grants-2011_08 |
|---|
| ORD ID | ord-c5ec82f2f0e94fb88539cfbec2b3ff8a |
|---|
| Source note | uspto-grants-2011_08 |
|---|
