1-[3-(3-(Pyridin-3-yl)phenyl)imidazo[1,2-alpha]pyridin-7-yl]ethanol → 1-[3-(3-(Pyridin-3-yl)phenyl)imidazo[1,2-alpha]pyridin-7-yl]ethanone

HRID 985521Notes

Reaction equation

[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([C:7]2[CH:8]=[C:9]([C:13]3[N:17]4[CH:18]=[CH:19][C:20]([CH:22]([OH:24])[CH3:23])=[CH:21][C:16]4=[N:15][CH:14]=3)[CH:10]=[CH:11][CH:12]=2)[CH:2]=1>ClCCCl.[O-2].[Mn+4].[O-2]>[NH3:1].[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([C:7]2[CH:8]=[C:9]([C:13]3[N:17]4[CH:18]=[CH:19][C:20]([C:22](=[O:24])[CH3:23])=[CH:21][C:16]4=[N:15][CH:14]=3)[CH:10]=[CH:11][CH:12]=2)[CH:2]=1

Participants

Conditions

Temperature: 50 °C

Procedure

1-[3-(3-(Pyridin-3-yl)phenyl)imidazo[1,2-α]pyridin-7-yl]ethanol (53 mg, 0.17 mmol) was suspended in 1,2-dichloroethane (2 ml), manganese(IV) oxide (73 mg, 0.84 mmol) added and the mixture heated at 50° C. for 18 h. The mixture was cooled to room temperature, filtered through Celite®, diluted with 1,2-dichloroethane and pre-adsorbed onto silica. Purification by silica gel chromatography eluting with dichloromethane/methanol/conc. ammonia (98:2:0.2) gave the title compound (44 mg, 85%) as a yellow solid. 1H NMR (400 MHz, CDCl3) δH 2.69 (3H, s), 7.40-7.48 (2H, m), 7.60-7.73 (3H, m), 7.77 (1H, d, J 1), 7.90-7.95 (2H, m), 8.30 (1H, s), 8.38 (1H, dd, J 1 and 7), 8.65-8.67 (1H, m), 8.91 (1H, s); m/z (ES+) 314 (M++H).

Workup

temperatureThe mixture was cooled to room temperature
filtrationfiltered through Celite®
additiondiluted with 1,2-dichloroethane and pre-adsorbed onto silica
customPurification by silica gel chromatography
washeluting with dichloromethane/methanol/conc

Sources & evidence

ORD record: ord-155df7c789a040749b296caf1450e191
Source dataset: uspto-grants-2005_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06872731B2

Reaction notes

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