2-((3-Bromo-5-iodopyridin-2-yl)oxy)ethanol → (E)-[5-Bromo-6-(2-hydroxyethoxy)pyridin-3-yl]-2-(4-methylaminophenyl)-ethylene
Reaction equation
[CH3:1][NH:2][C:3]1[CH:10]=[CH:9][C:6]([CH:7]=[CH2:8])=[CH:5][CH:4]=1.[OH:11][CH2:12][CH2:13][O:14][C:15]1[C:20]([Br:21])=[CH:19][C:18](I)=[CH:17][N:16]=1>>[Br:21][C:20]1[CH:19]=[C:18](/[CH:8]=[CH:7]/[C:6]2[CH:9]=[CH:10][C:3]([NH:2][CH3:1])=[CH:4][CH:5]=2)[CH:17]=[N:16][C:15]=1[O:14][CH2:13][CH2:12][OH:11]Participants
3
Procedure
Compound 14b was prepared from 4-methylaminostyrene (0.140 g, 1.05 mmol) and 9b (0.241 g, 0.7 mmol) as a light yellow viscous liquid (0.149 g, 61% yield). 1H NMR δ 8.07 (d, 1H, J=2.1 Hz), 8.03 (d, 1H, J=2.1 Hz), 7.35 (d, 2H, J=8.6 Hz), 6.93 (d, 1H, J=16.3 Hz), 6.74 (d, 1H, J=16.3 Hz), 6.61 (d, 2H, J=8.6 Hz), 4.57-4.52 (m, 2H), 3.99 (br s, 2H), 3.18 (br s, 1H), 2.88 (s, 3H). 13C NMR δ 149.6, 143.3, 138.5, 130.1, 130.0, 128.0, 126.0, 118.6, 112.6, 107.7, 69.8, 62.2, 30.7. HRMS calcd for C17H19BrN2O2 (M+), 348.0473; found, 348.0468.
Sources & evidence
- ORD record
- ord-2493699c42674d96ab8a7efa57b0cfb4
- Source dataset
- uspto-grants-2014_09
- Patent number
- US08840866B2
Reaction notes
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