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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 712651Generated: October 30, 2026

Dimethylamine → 2-(5-bromopyridin-3-yl)-N,N-dimethylacetamide

https://huagongshe.com/reaction/712651

Reaction equation

Participants

RoleNameHCIDCharge
ReactantDimethylamineHCID 674—
ReactantTriethylamineHCID 8471—
Reactant1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 15908—
Reactant1-HydroxybenzotriazoleHCID 75771—
Reactant2-(5-Bromopyridin-3-yl)acetic acidHCID 2802539—
SolventWaterHCID 962—
SolventDimethylformamideHCID 6228—
SolventDichloromethaneHCID 6344—
Product2-(5-bromopyridin-3-yl)-N,N-dimethylacetamideHCID 5378507979.6%

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

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS09181272B2
Source datasetuspto-grants-2015_11
ORD IDord-d51482cd99d744c6aff3a515b1a1aa39
Source noteuspto-grants-2015_11