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

HRID 77250Notes

Reaction equation

HRID 77250 reaction equation
[CH3:1][N:2]([CH3:11])[C:3]1[CH:10]=[CH:9][C:6]([CH:7]=[CH2:8])=[CH:5][CH:4]=1.[OH:12][CH2:13][CH2:14][O:15][C:16]1[C:21]([Br:22])=[CH:20][C:19](I)=[CH:18][N:17]=1>>[Br:22][C:21]1[CH:20]=[C:19](/[CH:8]=[CH:7]/[C:6]2[CH:9]=[CH:10][C:3]([N:2]([CH3:1])[CH3:11])=[CH:4][CH:5]=2)[CH:18]=[N:17][C:16]=1[O:15][CH2:14][CH2:13][OH:12]

Participants

3

Reactant 2

HCID 1372934-ethenyl-N,N-dimethylanilineHCID 162214442-((3-Bromo-5-iodopyridin-2-yl)oxy)ethanol

Product 1

HCID 16221511(E)-[5-Bromo-6-(2-hydroxyethoxy)pyridin-3-yl]-2-(4-dimethylaminophenyl)-ethylene

Procedure

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.

Sources & evidence

ORD record
ord-db62a6e5a1ee4a65a67baa539f261a9b
Source dataset
uspto-grants-2014_09
Patent number
US08840866B2

Reaction notes

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