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Sodium periodate → N-(3-ethyl-1-((6-formylpyridin-2-yl)methyl)-1H-indazol-4-yl)imidazo[1,2-a]pyridine-3-carboxamide

HRID 79290
Notes
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Reaction equation

HRID 79290 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]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 23667635Sodium periodateHCID 67260561N-(1-((6-(1,2-dihydroxyethyl)pyridin-2-yl)methyl)-3-ethyl-1H-indazol-4-yl)imidazo[1,2-a]pyridine-3-carboxamide

Product 1

HCID 86672209N-(3-ethyl-1-((6-formylpyridin-2-yl)methyl)-1H-indazol-4-yl)imidazo[1,2-a]pyridine-3-carboxamideYield 75%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

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

  1. stirringThe slurry was stirred for 30 minutes
  2. filtrationfiltered
  3. washwashed with dichloromethane (5 mL)
  4. concentrationThe solution was concentrated under reduced pressure

Sources & evidence

ORD record
ord-83bb3664ff1644938362974392f4a8a4
Source dataset
uspto-grants-2014_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08841455B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes