Dimethylamine → 3-bromo-N,N-dimethyl-5-(trifluoromethyl)pyridin-2-amine

Reaction equation

Cl[C:2]1[C:7]([Br:8])=[CH:6][C:5]([C:9]([F:12])([F:11])[F:10])=[CH:4][N:3]=1.[CH3:13][NH:14][CH3:15]>>[Br:8][C:7]1[C:2]([N:14]([CH3:15])[CH3:13])=[N:3][CH:4]=[C:5]([C:9]([F:12])([F:11])[F:10])[CH:6]=1

Participants

Reactant 2

HCID 674Dimethylamine

HCID 135360613-Bromo-2-chloro-5-(trifluoromethyl)pyridine

Product 1

HCID 220002253-bromo-N,N-dimethyl-5-(trifluoromethyl)pyridin-2-amineYield 82%

Procedure

2-Chloro-3-bromo-5-trifluoromethylpyridine (509 mg, 1.95 mmol) was treated with ethanolic dimethylamine solution (10 ml) and heated at reflux for 2 hrs before being concentrated. The residue was partitioned between water (10 ml) and ethyl acetate (10 ml), and the organic phase washed with brine (10 ml) and dried (Na2SO4). The solution was then concentrated to give the product as a yellow oil (430 mg, 82% yield).

Workup

temperatureheated
temperatureat reflux for 2 hrs
concentrationbefore being concentrated
customThe residue was partitioned between water (10 ml) and ethyl acetate (10 ml)
washthe organic phase washed with brine (10 ml)
dry with materialdried (Na2SO4)
concentrationThe solution was then concentrated

Sources & evidence

ORD record: ord-e0b49f56cb46443fb2047f51ce983857
Source dataset: uspto-grants-2001_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06225320B1

Reaction notes

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