HuagongsheHuagongshe Chemistry Print Report · For research reference only
Dimethylamine → 2-(5-bromopyridin-3-yl)-N,N-dimethylacetamide
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Dimethylamine | HCID 674 | — |
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | 1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide | HCID 15908 | — |
| Reactant | 1-Hydroxybenzotriazole | HCID 75771 | — |
| Reactant | 2-(5-Bromopyridin-3-yl)acetic acid | HCID 2802539 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | 2-(5-bromopyridin-3-yl)-N,N-dimethylacetamide | HCID 53785079 | 79.6% |
Reaction Steps
(5-Bromo-pyridin-3-yl)-acetic acid (200 mg, 0.93 mmol), 2.0 M dimethylamine solution (0.93 mL, 1.9 mmol), HOBt (25 mg, 0.19 mmol) and triethylamine (0.38 mL, 2.8 mmol) are dissolved in 5.0 mL of DMF. Then 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide (290 mg, 1.9 mmol) is added. The reaction mixture is stirred for 16 hrs before 30 mL of water and 30 mL of DCM are added. The aqueous layer is separated and extracted with DCM (4×10 mL). The organic layers are combined, dried and concentrated to give the crude product which is purified by flash chromatography to give 180 mg of 2-(5-bromo-pyridin-3-yl)-N,N-dimethyl-acetamide.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09181272B2 |
| Source dataset | uspto-grants-2015_11 |
| ORD ID | ord-d51482cd99d744c6aff3a515b1a1aa39 |
| Source note | uspto-grants-2015_11 |