HuagongsheHuagongshe Chemistry Print Report · For research reference only
Sodium Bicarbonate → (3-(trifluoromethyl)-5-((1-((3-(trifluoromethyl)pyridin-2-yl)methylamino)-2,3-dihydro-1H-inden-5-yl)methyl)phenyl)methanol
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Sodium Bicarbonate | HCID 516892 | — |
| Reactant | Sodium triacetoxyborohydride | HCID 5049666 | — |
| Reactant | 3-(Trifluoromethyl)pyridine-2-carboxaldehyde | HCID 14761470 | — |
| Reactant | HCID 66734486 | HCID 66734486 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | (3-(trifluoromethyl)-5-((1-((3-(trifluoromethyl)pyridin-2-yl)methylamino)-2,3-dihydro-1H-inden-5-yl)methyl)phenyl)methanol | HCID 86668750 | 45.7% |
Reaction Steps
Sodium triacetoxyborohydride (40 mg, 0.19 mmol) was added to a solution of (3-((1-amino-2,3-dihydro-1H-inden-5-yl)methyl)-5-(trifluoromethyl)phenyl)methanol (30 mg, 0.093) and 3-trifluoromethyl-2-formylpyridine (15 mg, 0.086 mmol) in DCM (1 mL). The reaction was stirred at rt for 24 h before aq. sat. NaHCO3 (2 mL) was added to the mixture was filtered over a phase separator. The organic filtrate was evaporated to dryness in a Genevac. The crude material was purified by prep. LCMS to afford the title compound (18.9 mg, 42.1%). MS (ESI): m/z [M+H]+ 481.2
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08633237B2 |
| Source dataset | uspto-grants-2014_01 |
| ORD ID | ord-b451a2d7c0db428090359e385cdbb507 |
| Source note | uspto-grants-2014_01 |