HuagongsheHuagongshe Chemistry Print Report · For research reference only
Diisopropylethylamine → Methyl 2-(trifluoromethyl)isonicotinate
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Diisopropylethylamine | HCID 81531 | — |
| Reactant | Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphate | HCID 151348 | — |
| Reactant | 2-(Trifluoromethyl)pyridine-4-carboxylic acid | HCID 14761447 | — |
| Solvent | Methanol | HCID 887 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | Methyl 2-(trifluoromethyl)isonicotinate | HCID 46311185 | 66% |
Reaction Steps
Under inert atmosphere, a mixture of 2-Trifluoromethyl-isonicotinic acid (1.0 equiv.), BOP (1.2 equiv.), DIPEA (1.5 equiv.) in DCM (C=0.1 molL−1) and MeOH (C=0.1 molL−1) was stirred at RT for 16 h. The reaction mixture was evaporated to dryness. The resulting residue was hydrolysed with HCl 1N and extracted twice with Et2O. The organic layers were combined, washed with a saturated solution of NaHCO3, brine, dried over MgSO4, concentrated to afford the product as transparent oil in a 66% yield.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09434734B2 |
| Source dataset | uspto-grants-2016_09 |
| ORD ID | ord-180c3ee89f924bc4b096cdf8b794aa59 |
| Source note | uspto-grants-2016_09 |