HuagongsheHuagongshe Chemistry Print Report · For research reference only
Triethylamine → HCID 131729501, compound
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | Sodium Hydroxide | HCID 14798 | — |
| Reactant | Trimethylsilylacetylene | HCID 66111 | — |
| Reactant | HCID 74931515 | HCID 74931515 | — |
| Catalyst | Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI) | HCID 24350 | — |
| Solvent | Methanol | HCID 887 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | HCID 131729501 | HCID 131729501 | 61.2% |
Reaction Steps
In a manner similar to the method described in example 6a, racemic(2′R, 3R, 4′S)-6-chloro-4′-(3-chlorophenyl)-2′-[5-iodo-2-(4-methoxy-phenoxy)-phenyl]spiro[3H-indole-3,3′-piperidine]-2,6′(1H)-dione (0.29 g, 0.42 mmol) was reacted with trimethylsilyl acetylene (0.41 g, 4.2 mmol), CuI (5 mg), triethylamine (1.76 mL, 12.7 mmol), and dichlorobis(triphenylphosphine) palladium (0) (23.4 mg, 0.034 mmol) in anhydrous N,N-dimethylformamide, and then treated with aqueous NaOH in methanol to give racemic(2′R, 3R, 4′S)-6-chloro-4′-(3-chlorophenyl)-2′-[5-ethynyl-2-(4-methoxy-phenoxy)-phenyl]spiro[3H-indole-3,3′-piperidine]-2,6′(1H)-dione as a white solid (Yield 0.15 g, 61%)
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08134001B2 |
| Source dataset | uspto-grants-2012_03 |
| ORD ID | ord-a051ea76956b4b4cb559b639a80f0cff |
| Source note | uspto-grants-2012_03 |