Chloroacetaldehyde → Methyl 8-chloro-5-(3-fluorophenyl)imidazo[1,2-a]pyridine-6-carboxylate

HRID 717829Notes

Reaction equation

HRID 717829 reaction equation
[NH2:1][C:2]1[C:11]([Cl:12])=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[C:4]([C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([F:19])[CH:14]=2)[N:3]=1.Cl[CH2:21][CH:22]=O.O>C(O)C>[Cl:12][C:11]1[C:2]2[N:3]([CH:21]=[CH:22][N:1]=2)[C:4]([C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([F:19])[CH:14]=2)=[C:5]([C:6]([O:8][CH3:9])=[O:7])[CH:10]=1

Participants

5

Reactant 3

HCID 33ChloroacetaldehydeHCID 962WaterHCID 58515985Methyl 6-amino-5-chloro-2-(3-fluorophenyl)nicotinate

Product 1

HCID 58515952Methyl 8-chloro-5-(3-fluorophenyl)imidazo[1,2-a]pyridine-6-carboxylateYield 87%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of methyl 6-amino-5-chloro-2-(3-fluorophenyl)nicotinate (0.19 g, 0.66 mmol) in ethanol (4 mL) at 60° C. was treated with 50 wt % chloroactaldehyde in water (0.34 mL, 2.6 mmol) dropwise. The reaction mixture was stirred at reflux for 2 hours. The reaction mixture was concentrated and purified by flash column chromatography with ethyl acetate in hexanes (0-60%) to give the desired product (180 mg, 87%). LCMS calculated for C15H11ClFN2O2 (M+H)+: m/z=305.0. found: 304.8.

Workup

  1. temperatureat reflux for 2 hours
  2. concentrationThe reaction mixture was concentrated
  3. custompurified by flash column chromatography with ethyl acetate in hexanes (0-60%)

Sources & evidence

ORD record
ord-365ab9f2fbb244d785831a65bdc955d8
Source dataset
uspto-grants-2015_11
Patent number
US09193721B2

Reaction notes

Loading…