Sodium sulfate decahydrate → 3-[3-(Pyridin-3-yl)phenyl]imidazo[1,2-alpha]pyridin-7-ylmethanol

HRID 985515Notes

Reaction equation

C[O:2][C:3]([C:5]1[CH:10]=[CH:9][N:8]2[C:11]([C:14]3[CH:19]=[CH:18][CH:17]=[C:16]([C:20]4[CH:21]=[N:22][CH:23]=[CH:24][CH:25]=4)[CH:15]=3)=[CH:12][N:13]=[C:7]2[CH:6]=1)=O.[H-].[Al+3].[Li+].[H-].[H-].[H-].O.O.O.O.O.O.O.O.O.O.S([O-])([O-])(=O)=O.[Na+].[Na+]>O1CCCC1.CO>[NH3:8].[N:22]1[CH:23]=[CH:24][CH:25]=[C:20]([C:16]2[CH:15]=[C:14]([C:11]3[N:8]4[CH:9]=[CH:10][C:5]([CH2:3][OH:2])=[CH:6][C:7]4=[N:13][CH:12]=3)[CH:19]=[CH:18][CH:17]=2)[CH:21]=1

Participants

Conditions

Temperature: 0 °C

Procedure

3-[3-(Pyridin-3-yl)phenyl]imidazo[1,2-α]pyridine-7-carboxylic acid methyl ester (2.0 g, 6.1 mmol) was suspended in tetrahydrofuran (75 ml) and cooled to 0° C. before adding lithium aluminium hydride (9.1 ml of 1.0M solution in tetrahydrofuran) dropwise over 5 minutes. The mixture was allowed to warm to ambient temperature and stirring continued for 2 h. Sodium sulphate decahydrate (10 g) was then added portionwise and the resulting suspension stirred for a further 1 h. The mixture was diluted with methanol and pre-adsorbed on to silica. Purification by flash column chromatography on silica eluting with dichloromethane/methanol/conc. ammonia (gradient 99:1:0.1 through to 95:5:0.3) gave the title compound (1.25 g, 68%) as a white solid. 1H NMR (360 MHz, CDCl3) δH 4.78 (2H, s), 6.87 (1H, dd, J 7 and 1), 7.37-7.43 (1H, m), 7.56-7.75 (6H, m), 7.89-7.95 (1H, m), 8.33 (1H, d, J 7), 8.63 (1H, dd, J 1 and 7), 8.89 (1H, s); m/z (ES+) 302 (M++H).

Workup

temperatureto warm to ambient temperature
stirringthe resulting suspension stirred for a further 1 h
customPurification by flash column chromatography on silica eluting with dichloromethane/methanol/conc

Sources & evidence

ORD record: ord-c8907a04f9d74828ae5f69a3d6f423ac
Source dataset: uspto-grants-2005_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06872731B2

Reaction notes

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