Potassium Carbonate → 5-(Imidazo[1,2-a]pyridin-8-ylmethoxy)-2-methoxybenzaldehyde

HRID 1473898Notes

Reaction equation

[OH:1][C:2]1[CH:3]=[CH:4][C:5]([O:10][CH3:11])=[C:6]([CH:9]=1)[CH:7]=[O:8].Cl[CH2:13][C:14]1[C:15]2[N:16]([CH:20]=[CH:21][N:22]=2)[CH:17]=[CH:18][CH:19]=1.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[N:22]1[CH:21]=[CH:20][N:16]2[CH:17]=[CH:18][CH:19]=[C:14]([CH2:13][O:1][C:2]3[CH:3]=[CH:4][C:5]([O:10][CH3:11])=[C:6]([CH:9]=3)[CH:7]=[O:8])[C:15]=12

Participants

Conditions

Temperature: 125 °C

Procedure

A mixture of 5-hydroxy-2-methoxybenzaldehyde (723.6 mg, 4.7 mmol), 8-(chloromethyl)-imidazol[1,2-a]pyridine (785 mg, 4.7 mmol), and K2CO3 (1.9 g, 14.1 mmol) in DMF (20 mL) was heated at microwave reactor at 125° C. for 15 min. The mixture was filtered and concentrated. The residue was purified on silica gel (50-100% EtOAc in hexanes) to give 5-(imidazo[1,2-a]pyridin-8-ylmethoxy)-2-methoxybenzaldehyde.

Workup

filtrationThe mixture was filtered
concentrationconcentrated
customThe residue was purified on silica gel (50-100% EtOAc in hexanes)

Sources & evidence

ORD record: ord-0e8a0949e989490bae550f01d66a4061
Source dataset: uspto-grants-2015_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09018210B2

Reaction notes

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