3-[3-(Pyridin-3-yl)phenyl]imidazo[1,2-alpha]pyridin-7-ylmethanol → 3-[3-(Pyridin-3-yl)phenyl]imidazo[1,2-alpha]pyridine-7-carboxaldehyde

HRID 985516Notes

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]([CH2:22][OH: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]([CH:22]=[O: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

A suspension of 3-[3-(pyridin-3-yl)phenyl]imidazo[1,2-α]pyridin-7-ylmethanol (67 mg, 0.22 mmol) in 1,2-dichloroethane (5 ml) was treated with manganese(IV) oxide (0.19 g, 2.2 mmol) and the mixture heated at 50° C. for 18 h. The reaction was cooled to ambient temperature, diluted with 1,2-dichloroethane and pre-adsorbed onto silica. Purification by silica gel chromatography eluting with dichloromethane/methanol/conc. ammonia (95:5:0.5) gave the title compound (38 mg, 58%) as a yellow solid. 1H NMR (360 MHz, CDCl3) δH 7.36-7.45 (2H, m), 7.60-7.73 (3H, m), 7.76-7.78 (1H, m), 7.90-7.95 (1H, m), 7.97 (1H, s), 8.20 (1H, s), 8.40 (1H, d, J 7), 8.65 (1H, d, J 5), 8.90 (1H, s), 10.00 (1H, s); m/z (ES+) 300 (M++H).

Workup

temperatureThe reaction was cooled to ambient temperature
customPurification by silica gel chromatography
washeluting with dichloromethane/methanol/conc

Sources & evidence

ORD record: ord-b523f04a36794f72bc9d826cd9bd101f
Source dataset: uspto-grants-2005_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06872731B2

Reaction notes

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