2-Amino-5-fluoropyridine → Ethyl 6-fluoroimidazo[1,2-a]pyridine-3-carboxylate

HRID 706732Notes

Reaction equation

HRID 706732 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]([NH2:8])=[N:6][CH:7]=1.Cl[CH:10]([C:16](Cl)=O)[C:11]([O:13][CH2:14][CH3:15])=[O:12]>C(O)C>[F:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([C:10]([C:11]([O:13][CH2:14][CH3:15])=[O:12])=[CH:16][N:8]=2)[CH:7]=1

Participants

4

Reactant 2

HCID 27377012-Amino-5-fluoropyridineHCID 86699347Ethyl 2,3-dichloro-3-oxopropanoate

Product 1

HCID 67976050Ethyl 6-fluoroimidazo[1,2-a]pyridine-3-carboxylateYield 5.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

5-Fluoropyridine-2-amine (1 g, 8.92 mmol) and ethyl 2,3-dichloro-3-oxopropanoate (39.6 g, 10.7 mmol, 5% in benzene) were added to a flask along with 75 mL of ethanol and stirred overnight at ambient temperature. The material was purified on Silica gel using methanol and ethyl acetate (Rf=0.4 in 5% MeOH/ethyl acetate) to provide 110 mg of the desired compound as a waxy solid, 95% pure by LC. MS (ES+APCI) m/z=209.2 (M+H).

Workup

  1. customThe material was purified on Silica gel

Sources & evidence

ORD record
ord-39f8d0a5020d451699a52996471e7e1d
Source dataset
uspto-grants-2015_11
Patent number
US09174981B2

Reaction notes

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