Iodoacetamide → HCID 15037309, compound

HRID 1607444Notes

Reaction equation

HRID 1607444 reaction equation
CO[C:3]([CH:5]1[C:17]2[C:12](=[N:13][CH:14]=[C:15]([F:18])[CH:16]=2)[C:11]2[C:6]1=[CH:7][C:8]([F:20])=[CH:9][C:10]=2[CH3:19])=[O:4].[H-].[Na+].I[CH2:24][C:25]([NH2:27])=[O:26]>O1CCCC1>[F:18][C:15]1[CH:16]=[C:17]2[C:5]3([CH2:24][C:25](=[O:26])[NH:27][C:3]3=[O:4])[C:6]3[C:11](=[C:10]([CH3:19])[CH:9]=[C:8]([F:20])[CH:7]=3)[C:12]2=[N:13][CH:14]=1

Participants

5

Reactant 3

HCID 3727IodoacetamideHCID 24758Sodium hydrideHCID 67903145HCID 67903145, compound

Product 1

HCID 15037309HCID 15037309, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Treatment of 3,7-difluoro-9-methyl-5H-indeno[1,2-b]pyridin-5-one with hydrazine in hot diethylene glycol provided 3,7-difluoro-9-methyl-5H-indeno[1,2-b]pyridine. Deprotonation using n-butyllithium in tetrahydrofuran followed by reaction with carbon dioxide and methanolic hydrogen chloride provided 3,7-difluoro-9-methyl-5H-indeno[1,2-b]pyridin-5-carboxylic acid methyl ester. The ester was then deprotonated using a slight excess of sodium hydride in tetrahydrofuran and treated with iodoacetamide to provide, after 18 hours at room temperature and 6 hours at reflux, the title compound.

Workup

  1. customto provide, after 18 hours at room temperature and 6 hours
  2. temperatureat reflux

Sources & evidence

ORD record
ord-e4a7e38d76454ef38e1ee0ec9921036a
Source dataset
uspto-grants-1989_09
Patent number
US04864028

Reaction notes

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