2,4-Dimethoxybenzylamine → HCID 89545592, compound

HRID 2203420Notes

Reaction equation

HRID 2203420 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([C:8]([C:11]([O:13]CC)=O)=[CH:9][N:10]=2)[CH:7]=1.[CH3:16][O:17][C:18]1[CH:25]=[C:24]([O:26][CH3:27])[CH:23]=[CH:22][C:19]=1[CH2:20][NH2:21]>C1(C)C=CC=CC=1>[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([C:8]([C:11]([NH:21][CH2:20][C:19]3[CH:22]=[CH:23][C:24]([O:26][CH3:27])=[CH:25][C:18]=3[O:17][CH3:16])=[O:13])=[CH:9][N:10]=2)[CH:7]=1

Participants

4

Reactant 2

HCID 5972502,4-DimethoxybenzylamineHCID 22031055Ethyl 6-bromoimidazo[1,2-a]pyridine-3-carboxylate

Product 1

HCID 89545592HCID 89545592, compoundYield 20%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
120 °C

Procedure

To a solution of ethyl 6-bromoimidazo[1,2-a]pyridine-3-carboxylate (1.0 g, 3.7 mmol) in toluene (5 mL) was added 2,4-dimethoxybenzylamine (0.93 g, 5.6 mmol). The reaction mixture was heated at 120° C. for 2 days in a sealed tube, allowed to cool to ambient temperature and concentrated in vacuo. The residue was purified by column chromatography eluting with a 0-100% gradient of ethyl acetate in hexanes to afford 6-bromo-N-(2,4-dimethoxybenzyl)imidazo[1,2-a]pyridine-3-carboxamide as a yellow oil in 20% yield (0.29 g): 1H NMR (300 MHz, CDCl3) δ9.70-9.67 (m, 1H), 7.91 (s, 1H), 7.53 (dd, J=9.5, 0.7 Hz, 1H), 7.38 (dd, J=9.5, 1.9 Hz, 1H), 7.27-7.21 (m, 2H), 6.48-6.38 (m, 2H), 4.54 (d, J=5.8 Hz, 2H), 3.85 (s, 3H), 3.78 (s, 3H); MS (ES+) m/z 389.8 (M+1), 391.8 (M+1).

Workup

  1. temperatureto cool to ambient temperature
  2. concentrationconcentrated in vacuo
  3. customThe residue was purified by column chromatography
  4. washeluting with a 0-100% gradient of ethyl acetate in hexanes

Sources & evidence

ORD record
ord-57af532ffc6e46b9a51c90fb03e3cff0
Source dataset
uspto-grants-2016_06
Patent number
US09365578B2

Reaction notes

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