4-ethenyl-N,N-dimethylaniline → (E)-[5-Bromo-6-(2-hydroxyethoxy)pyridin-3-yl]-2-(4-dimethylaminophenyl)-ethylene

Participants

Role	Name	HCID	Charge
Reactant	4-ethenyl-N,N-dimethylaniline	HCID 137293	—
Reactant	2-((3-Bromo-5-iodopyridin-2-yl)oxy)ethanol	HCID 16221444	—
Product	(E)-[5-Bromo-6-(2-hydroxyethoxy)pyridin-3-yl]-2-(4-dimethylaminophenyl)-ethylene	HCID 16221511	—

Reaction Steps

Compound 14a was prepared from 4-dimethylaminostyrene (0.031 g, 0.212 mmol) and 9b (0.073 g, 0.212 mmol) as a light yellow solid (0.022 g, 29% yield). 1H NMR δ 8.07 (d, 1H, J=2.1 Hz), 8.03 (d, 1H, J=2.1 Hz), 7.39 (d, 2H, J=8.8 Hz), 6.94 (d, 1H, J=16.3 Hz), 6.78-6.69 (m, 3H), 4.57-4.52 (m, 2H), 3.99 (t, 2H, J=4.3 Hz), 3.21 (br s, 1H), 3.00 (s, 6H). 13C NMR δ 158.3, 150.4, 143.0, 138.2, 129.9, 129.8, 127.6, 124.9, 118.3, 112.3, 107.5, 69.6, 62.1, 40.3. HRMS calcd for C17H19BrN2O2 (M+), 362.063; found, 362.0629.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08840866B2
Source dataset	uspto-grants-2014_09
ORD ID	ord-db62a6e5a1ee4a65a67baa539f261a9b
Source note	uspto-grants-2014_09