Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | Triphenylphosphine | HCID 11776 | — |
| Reactant | Sodium Azide | HCID 33557 | — |
| Reactant | Di-tert-butyl dicarbonate | HCID 90495 | — |
| Reactant | (cis-1-(benzyl(methyl)amino)-7-bromo-2,3-dihydro-1H-pyrrolo[1,2-a]indol-2-yl)methyl methanesulfonate | HCID 89422947 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | HCID 131736657 | HCID 131736657 | 35% |
Reaction Steps
The crude material from Step 3 was dissolved in DMF (5 mL) and treated with NaN3 (234 mg, 3.6 mmol). The mixture was heated at 80° C. for 2 h. To the mixture was added H2O (1 mL) and triphenylphosphine (524 mg, 2 mmol). The mixture stirred at 80° C. for 1 h. After cooling the mixture to room temperature, triethylamine (0.5 mL, 3.6 mmol) and di-tert-butyldicarbonate (436 mg, 2.0 mmol) were added sequentially. The mixture was stirred at room temperature for 1 h. The mixture was concentrated and chromatographed on silica gel (0-8% MeOH in CH2Cl2) to afford the product (300 mg, 35%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US09409905B2 |
|---|
| Source dataset | uspto-grants-2016_08 |
|---|
| ORD ID | ord-c39bee68940a49808ca7a3fad1ae913e |
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| Source note | uspto-grants-2016_08 |
|---|
