2-Bromopyridine → 2-(2-Dimethylamino-ethoxy)-5-pyridin-2-yl-benzaldehyde

HRID 30617Notes

Reaction equation

HRID 30617 reaction equation
[CH3:1][N:2]([CH3:17])[CH2:3][CH2:4][O:5][C:6]1[CH:11]=[CH:10][C:9](B(O)O)=[CH:8][C:7]=1[CH:15]=[O:16].Br[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][N:20]=1>>[CH3:1][N:2]([CH3:17])[CH2:3][CH2:4][O:5][C:6]1[CH:11]=[CH:10][C:9]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][N:20]=2)=[CH:8][C:7]=1[CH:15]=[O:16]

Participants

3

Reactant 2

HCID 79732-BromopyridineHCID 858888554-(2-Dimethylamino-ethoxy)-3-formyl-benzeneboronic acid

Product 1

HCID 858888752-(2-Dimethylamino-ethoxy)-5-pyridin-2-yl-benzaldehydeYield 40%

Procedure

General procedure G using 4-(2-dimethylamino-ethoxy)-3-formyl-benzeneboronic acid and 2-bromo-pyridine gave the title product as yellow oil in 40% yield. 1H-NMR (CDCl3) δ 10.47 (s, 1H), 8.60(dt, 1H), 8.34 (d, 1H), 8.26 (dd, 1H), 7.69-7.67 (m, 2H), 7.17-7.14 (m, 1H), 7.05 (d, 1H), 4.24 (t, 2H), 2.83 (t, 2H), 2.36 (s, 6H).

Sources & evidence

ORD record
ord-baa2a12fddac400698f89e2fa85b83d6
Source dataset
uspto-grants-2008_09
Patent number
US07423181B2

Reaction notes

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