Hydrochloric Acid → 7-Fluoro-1H-pyrrolo[3,2-C]pyridine
Reaction equation
C(O[CH:4]=[CH:5][C:6]1[CH:7]=[N:8][CH:9]=[C:10]([F:13])[C:11]=1[NH2:12])C.Cl>CCO>[F:13][C:10]1[C:11]2[NH:12][CH:4]=[CH:5][C:6]=2[CH:7]=[N:8][CH:9]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
A mixture of 3-(2-ethoxy-vinyl)-5-fluoro-pyridin-4-ylamine (Preparation 63, 3.6 g, 19.2 mmol) and concentrated HCl (10 mL) in EtOH (44 mL) was heated to reflux for 4 hours before cooling and concentrating in vacuo. The residue was basified with saturated aqueous NaHCO3 solution, extracted in DCM, the organic layer collected, dried over sodium sulphate and concentrated in vacuo. The residue was purified using silica gel column chromatography eluting with 20-100% EtOAc in hexane to afford the title compound (1.7 g)
Workup
- temperaturewas heated
- temperatureto reflux for 4 hours
- temperaturebefore cooling
- concentrationconcentrating in vacuo
- extractionextracted in DCM
- customthe organic layer collected
- dry with materialdried over sodium sulphate
- concentrationconcentrated in vacuo
- customThe residue was purified
- washeluting with 20-100% EtOAc in hexane
Sources & evidence
- ORD record
- ord-996d3db6451549c5aafd800d14c8c6ae
- Source dataset
- uspto-grants-2015_10
- Patent number
- US09163021B2
Reaction notes
Loading…