Phosphorus oxychloride → Methyl 6-chloro-4-cyano-2-(1-ethyl-1H-pyrazol-4-yl)nicotinate

HRID 711515Notes

Reaction equation

HRID 711515 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][N+:6]([O-])=[C:5]([C:10]2[CH:11]=[N:12][N:13]([CH2:15][CH3:16])[CH:14]=2)[C:4]=1[C:17]([O:19][CH3:20])=[O:18])#[N:2].O=P(Cl)(Cl)[Cl:23]>>[Cl:23][C:7]1[CH:8]=[C:3]([C:1]#[N:2])[C:4]([C:17]([O:19][CH3:20])=[O:18])=[C:5]([C:10]2[CH:11]=[N:12][N:13]([CH2:15][CH3:16])[CH:14]=2)[N:6]=1

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 672385264-Cyano-2-(1-ethyl-1H-pyrazol-4-yl)-3-(methoxycarbonyl)pyridine 1-oxide

Product 1

HCID 58317713Methyl 6-chloro-4-cyano-2-(1-ethyl-1H-pyrazol-4-yl)nicotinateYield 90%

Procedure

A solution of 4-cyano-2-(1-ethyl-1H-pyrazol-4-yl)-3-(methoxycarbonyl)pyridine 1-oxide (210 mg, 0.771 mmol) in POCl3 (2 mL) was heated at 80° C. for 3-4 h. The mixture was concentrated and purified by flash chromatography (SiO2, 10-100% EtOAc in Hexane). The fractions were collected and the solvent was removed in vacuo to give the title compound (201 mg, 90%).

Workup

  1. concentrationThe mixture was concentrated
  2. custompurified by flash chromatography (SiO2, 10-100% EtOAc in Hexane)
  3. customThe fractions were collected
  4. customthe solvent was removed in vacuo

Sources & evidence

ORD record
ord-04a8a5b3152b47c989464c76a3607076
Source dataset
uspto-grants-2015_11
Patent number
US09181255B2

Reaction notes

Loading…