Dimethylformamide → Imidazo[1,2-a]pyridine-3-carbonyl Chloride

HRID 335333Notes

Reaction equation

HRID 335333 reaction equation
[N:1]1[CH:2]=[C:3]([C:10]([OH:12])=O)[N:4]2[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=12.C(Cl)(=O)C([Cl:16])=O.CN(C=O)C>C(Cl)Cl>[N:1]1[CH:2]=[C:3]([C:10]([Cl:16])=[O:12])[N:4]2[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=12

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 65578Oxalyl chlorideHCID 73142Imidazo(1,2-a)pyridine-3-carboxylic acid

Product 1

HCID 74890117Imidazo[1,2-a]pyridine-3-carbonyl Chloride

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A suspension of imidazo[1,2-a]pyridine-3-carboxylic acid (5.270 g, 32.5 mmol) in DCM (200 ml) was treated with oxalyl chloride (3.13 ml, 35.8 mmol) followed by the addition of DMF (0.252 ml, 3.25 mmol). The reaction mixture was stirred at RT overnight. The solvent was removed in vacuo to afford the title compound as a hydrochloride salt;

Workup

  1. customThe solvent was removed in vacuo

Sources & evidence

ORD record
ord-122103a473254fb99f822a83836a206f
Source dataset
uspto-grants-2014_11
Patent number
US08883819B2

Reaction notes

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