HuagongsheHuagongshe Chemistry Print Report · For research reference only
Dimethylformamide → 5-Bromo-N-cyclopropylpyridine-2-carboxamide
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Dimethylformamide | HCID 6228 | — |
| Reactant | Cyclopropylamine | HCID 69828 | — |
| Reactant | Diisopropylethylamine | HCID 81531 | — |
| Reactant | Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphate | HCID 151348 | — |
| Reactant | 5-Bromopyridine-2-carboxylic acid | HCID 608544 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | 5-Bromo-N-cyclopropylpyridine-2-carboxamide | HCID 26370089 | — |
Reaction Steps
N,N-Diisopropylethylamine (0.69 mL, 0.0040 mol) was added to a mixture of 5-bromopyridine-2-carboxylic acid (400 mg, 0.002 mol), cyclopropylamine (0.16 mL, 0.0024 mol) and benzotriazol-1-yloxytris(dimethylamino)phosphonium hexafluorophosphate (1.1 g, 0.0024 mol) in N,N-dimethylformamide (9.4 mL, 0.12 mol) at 0° C. and the mixture was stirred overnight at room temperature. The mixture was diluted with ethyl acetate, washed with water and brine successively, dried over sodium sulfate, filtered and concentrated. The product was purified by CombiFlash eluting with CH2Cl2/EtOAc (max.EtOAc 20%). LC-MS: 241.1/243.1 (M+H+)
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08058288B2 |
| Source dataset | uspto-grants-2011_11 |
| ORD ID | ord-608f3976613242cc85a4cb23aedc7b10 |
| Source note | uspto-grants-2011_11 |