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

HRID 1473887Notes

Reaction equation

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

Participants

Conditions

Temperature: 87.5 °C

Procedure

To a solution of the crude 8-(chloromethyl)imidazo[1,2-a]pyridine (6.8 mmol, 1 eq) and 2-hydroxy-5-methoxybenzaldehyde (1.3 g, 8.1 mmol, 1.2 eq) in DMF (20 mL) was added potassium carbonate (2.8 g, 20.4 mmol, 3 eq) and the reaction mixture was heated at 85-90° C. for 5 h. DMF was removed under vacuum and the residue was taken in ethyl acetate and filtered. The solid was washed with additional ethyl acetate, and then dried and evaporated to give the crude, which was purified by column chromatography (EtOAc/Hexane) to yield the desired compound in 45% yield. NMR (400 MHz, CDCl3): δ 3.80 (s, 3H), 5.60 (s, 2H), 6.85 (d, 1H), 7.12 (d, 2H), 7.36 (m, 2H), 7.66 (m, 2H), 8.14 (m, 1H), 10.58 (s, 1H); MS: exact mass calculated for C16H14N2O3, 282.10; m/z found, 283 [M+H]+.

Workup

customDMF was removed under vacuum
filtrationfiltered
washThe solid was washed with additional ethyl acetate
customdried
customevaporated
customto give the crude, which
customwas purified by column chromatography (EtOAc/Hexane)

Sources & evidence

ORD record: ord-0eb5b9b6080743bdb70dd0e756544964
Source dataset: uspto-grants-2015_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09018210B2

Reaction notes

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