Sodium periodate → N-(3-ethyl-1-((6-formylpyridin-2-yl)methyl)-1H-indazol-4-yl)imidazo[1,2-a]pyridine-3-carboxamide
Reaction equation
I([O-])(=O)(=O)=O.[Na+].[OH:7][CH:8]([C:11]1[N:16]=[C:15]([CH2:17][N:18]2[C:26]3[C:21](=[C:22]([NH:27][C:28]([C:30]4[N:34]5[CH:35]=[CH:36][CH:37]=[CH:38][C:33]5=[N:32][CH:31]=4)=[O:29])[CH:23]=[CH:24][CH:25]=3)[C:20]([CH2:39][CH3:40])=[N:19]2)[CH:14]=[CH:13][CH:12]=1)CO>ClCCl>[CH2:39]([C:20]1[C:21]2[C:26](=[CH:25][CH:24]=[CH:23][C:22]=2[NH:27][C:28]([C:30]2[N:34]3[CH:35]=[CH:36][CH:37]=[CH:38][C:33]3=[N:32][CH:31]=2)=[O:29])[N:18]([CH2:17][C:15]2[CH:14]=[CH:13][CH:12]=[C:11]([CH:8]=[O:7])[N:16]=2)[N:19]=1)[CH3:40]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
To a slurry of silica gel (200 mg) in dichloromethane (1 mL) was added, drop wise, sodium periodate solution (202 μL, 0.13 mmol; 0.65M in water). The slurry was stirred for 10 minutes and broken up into a fine slurry with a spatula. To this was slowly added N-(1-((6-(1,2-dihydroxyethyl)pyridin-2-yl)methyl)-3-ethyl-1H-indazol-4-yl)imidazo[1,2-a]pyridine-3-carboxamide (40 mg, 0.088 mmol) in dichloromethane (1 mL). The slurry was stirred for 30 minutes, then filtered and washed with dichloromethane (5 mL). The solution was concentrated under reduced pressure to provide the desired product (28 mg).
Workup
- stirringThe slurry was stirred for 30 minutes
- filtrationfiltered
- washwashed with dichloromethane (5 mL)
- concentrationThe solution was concentrated under reduced pressure
Sources & evidence
- ORD record
- ord-83bb3664ff1644938362974392f4a8a4
- Source dataset
- uspto-grants-2014_09
- Patent number
- US08841455B2
Reaction notes
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