Potassium Carbonate → HCID 86690759, compound

HRID 1471717Notes

Reaction equation

HRID 1471717 reaction equation
[N:1]1[CH:2]=[CH:3][N:4]2[CH:9]=[CH:8][CH:7]=[C:6]([CH2:10][O:11][C:12]3[C:13]([CH:19]=[O:20])=[CH:14][C:15](=[O:18])[NH:16][CH:17]=3)[C:5]=12.C([O-])([O-])=O.[K+].[K+].Br[CH2:28][CH2:29][O:30][CH3:31]>CN(C=O)C>[N:1]1[CH:2]=[CH:3][N:4]2[CH:9]=[CH:8][CH:7]=[C:6]([CH2:10][O:11][C:12]3[C:13]([CH:19]=[O:20])=[CH:14][C:15]([O:18][CH2:28][CH2:29][O:30][CH3:31])=[N:16][CH:17]=3)[C:5]=12

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 809722-Bromoethyl methyl etherHCID 71620964HCID 71620964, compound

Product 1

HCID 86690759HCID 86690759, compoundYield 5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a mixture of 5-(imidazo[1,2-a]pyridin-8-ylmethoxy)-2-oxo-1,2-dihydropyridine-4-carbaldehyde (100 mg, 0.37 mmol, 1 equiv) and K2CO3 (153.2 mg, 1.11, 3.0 eq.) in DMF (5 mL) was added 1-bromo-2-methoxyethane (154.3 mg, 1.11 mmol, 3.0 eq.). The mixture was stirred at rt O/N, filtered, concentrated, and purified on silica gel using 10% MeOH/DCM as eluent to give 5-(imidazo[1,2-a]pyridin-8-ylmethoxy)-2-(2-methoxyethoxy)isonicotinaldehyde (6.0 mg, 5%) as an yellow solid. 1H NMR (400 MHz, CDCl3) δ 10.45 (s, 1H), 8.08 (d, J=6.8 Hz, 1H), 8.06 (s, 1H), 7.60 (dd, J=6.8, 1.2 Hz, 2H), 7.27 (dd, J=6.9, 1.0 Hz, 1H), 7.09 (s, 1H), 6.78 (t, J=6.9 Hz, 1H), 5.58 (s, 2H), 4.35 (dd, J=5.4, 3.9 Hz, 2H), 3.66 (dd, J=5.4, 3.9 Hz, 2H), 3.36 (s, 3H). LRMS (M+H+) m/z 328.1.

Workup

  1. filtrationfiltered
  2. concentrationconcentrated
  3. custompurified on silica gel using 10% MeOH/DCM as eluent

Sources & evidence

ORD record
ord-e20e0e2378f3438eb5a1c3001b65a1d8
Source dataset
uspto-grants-2015_04
Patent number
US09012450B2

Reaction notes

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