Water → 5-((2-Bromopyridin-3-yl)methoxy)-2-methoxyisonicotinaldehyde

HRID 1471685Notes

Reaction equation

HRID 1471685 reaction equation
[OH:1][C:2]1[C:7]([CH:8]=[O:9])=[CH:6][C:5]([O:10][CH3:11])=[N:4][CH:3]=1.[Br:12][C:13]1[C:18]([CH2:19]Cl)=[CH:17][CH:16]=[CH:15][N:14]=1.C([O-])([O-])=O.[K+].[K+].O>CN(C=O)C>[Br:12][C:13]1[C:18]([CH2:19][O:1][C:2]2[C:7]([CH:8]=[O:9])=[CH:6][C:5]([O:10][CH3:11])=[N:4][CH:3]=2)=[CH:17][CH:16]=[CH:15][N:14]=1

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 534166322-Bromo-3-(chloromethyl)pyridineHCID 722124985-Hydroxy-2-methoxyisonicotinaldehyde

Product 1

HCID 716217595-((2-Bromopyridin-3-yl)methoxy)-2-methoxyisonicotinaldehydeYield 85%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of 5-hydroxy-2-methoxyisonicotinaldehyde (306 mg, 2 mmol, 1 eq.), 2-bromo-3-(chloromethyl)pyridine (crude above, 2 mmol), and K2CO3 (828 mg, 6 mmol, 3 eq.) in DMF (1.0 mL) was heated at 50° C. for 2 h. The mixture was cooled and added to water (50 mL) dropwise. The precipitate was filtered, washed with water, dried under high vacuo to give 5-((2-bromopyridin-3-yl)methoxy)-2-methoxyisonicotinaldehyde (350 mg, 85%) as an yellow solid. 1H NMR (400 MHz; CDCl3) δ=10.51 (s, 1H), 8.42 (dd, 1H), 8.09 (s, 1H) 7.91 (d, 1H), 7.40 (dd, 1H), 7.15 (s, 1H), 5.27 (s, 2H), 3.95 (s, 3H). LRMS (M+H+) m/z 323.0.

Workup

  1. temperatureThe mixture was cooled
  2. filtrationThe precipitate was filtered
  3. washwashed with water
  4. customdried under high vacuo

Sources & evidence

ORD record
ord-86d8c62151ba41db91a9412daacb2a39
Source dataset
uspto-grants-2015_04
Patent number
US09012450B2

Reaction notes

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