5-Bromo-2,4-dimethoxybenzaldehyde → 2,4-Dimethoxy-5-pyridin-3-yl-benzaldehyde

HRID 10726Notes

Reaction equation

HRID 10726 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3](B(O)O)[CH:2]=1.Br[C:11]1[C:12]([O:21][CH3:22])=[CH:13][C:14]([O:19][CH3:20])=[C:15]([CH:18]=1)[CH:16]=[O:17]>>[CH3:20][O:19][C:14]1[CH:13]=[C:12]([O:21][CH3:22])[C:11]([C:3]2[CH:2]=[N:1][CH:6]=[CH:5][CH:4]=2)=[CH:18][C:15]=1[CH:16]=[O:17]

Participants

3

Reactant 2

HCID 6683465-Bromo-2,4-dimethoxybenzaldehydeHCID 27343783-Pyridinylboronic acid

Product 1

HCID 219811132,4-Dimethoxy-5-pyridin-3-yl-benzaldehydeYield 68%

Procedure

Ex-104A: 2,4-Dimethoxy-5-pyridin-3-yl-benzaldehyde was prepared in a similar manner as described in Ex-3A from pyridine-3-boronic acid and 5-bromo-2,4-dimethoxybenzaldehyde, 68% yield. 1H-NMR (CDCl3) δ 10.33 (s, 1H), 8.71 (d, J=1 Hz, 1H), 8.51–8.53 (m, 1H), 7.81 (s, 1H), 7.74–7.78 (m, 1H), 7.27–7.31 (m, 1H), 6.52 (s, 1H), 3.99 (s, 3H), 3.91 (s, 3H). HMRS (EI) calcd. for C14H13NO3: 243.0895; found: 243.0888.

Sources & evidence

ORD record
ord-fd3f66696ce2493987252185d90a7bbb
Source dataset
uspto-grants-2006_08
Patent number
US07094801B2

Reaction notes

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