Dimethylformamide → HCID 86717885, compound

HRID 923505Notes

Reaction equation

HRID 923505 reaction equation
[F:1][C:2]1[CH:22]=[CH:21][CH:20]=[C:19]([F:23])[C:3]=1[CH2:4][O:5][C:6]1[C:7]2[N:8]([C:12]([C:16](O)=[O:17])=[C:13]([CH3:15])[N:14]=2)[CH:9]=[CH:10][CH:11]=1.CN(C=O)C.C(Cl)(=O)C([Cl:32])=O>ClCCl>[ClH:32].[F:1][C:2]1[CH:22]=[CH:21][CH:20]=[C:19]([F:23])[C:3]=1[CH2:4][O:5][C:6]1[C:7]2[N:8]([C:12]([C:16]([Cl:32])=[O:17])=[C:13]([CH3:15])[N:14]=2)[CH:9]=[CH:10][CH:11]=1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 65578Oxalyl chlorideHCID 867178728-((2,6-Difluorobenzyl)oxy)-2-methylimidazo[1,2-a]pyridine-3-carboxylic acid

Product 1

HCID 86717885HCID 86717885, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Under an argon gas flow, to a suspension of 32.5 g of 8-[(2,6-difluorobenzyl)oxy]-2-methylimidazo[1,2-a]pyridine-3-carboxylic acid in 807 ml of dichloromethane were added 190 μl of DMF and 17.2 ml of oxalyl chloride under ice-cooling, followed by stirring at room temperature for 80 minutes. The reaction mixture was concentrated under reduced pressure to obtain 38.0 g of 8-[(2,6-difluorobenzyl)oxy]-2-methylimidazo[1,2-a]pyridine-3-carbonyl chloride hydrochloride.

Workup

  1. temperaturecooling
  2. concentrationThe reaction mixture was concentrated under reduced pressure

Sources & evidence

ORD record
ord-0029bbc49be84fda99bbeef8f0bdb171
Source dataset
uspto-grants-2016_03
Patent number
US09278968B2

Reaction notes

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