Phosphorus oxychloride → 5-Chloro-7-(4-(trifluoromethoxy)phenyl)-1,6-naphthyridine

HRID 715703Notes

Reaction equation

HRID 715703 reaction equation
F[C:2]1[CH:3]=[C:4]([C:13]2[N:14]=[C:15](O)[C:16]3[CH:17]=[CH:18][CH:19]=[N:20][C:21]=3[CH:22]=2)[CH:5]=[CH:6][C:7]=1[O:8][C:9]([F:12])([F:11])[F:10].P(Cl)(Cl)([Cl:26])=O>C(N(CC)C1C=CC=CC=1)C>[Cl:26][C:15]1[N:14]=[C:13]([C:4]2[CH:5]=[CH:6][C:7]([O:8][C:9]([F:12])([F:11])[F:10])=[CH:2][CH:3]=2)[CH:22]=[C:21]2[C:16]=1[CH:17]=[CH:18][CH:19]=[N:20]2

Participants

4

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 178517527HCID 178517527, compound

Product 1

HCID 866615735-Chloro-7-(4-(trifluoromethoxy)phenyl)-1,6-naphthyridine

Reagents, catalysts & solvents 1

HCID 7061N,N-DiethylanilineSolvent

Procedure

200 mg 7-(3-fluoro-4-trifluormethoxy-phenyl)[1,6]-naphthyridine-5-ol (5.1) and 10 μL N,N-diethylaniline were stirred into 4 mL phosphorus oxychloride overnight at 120° C. The reaction mixture was evaporated down, followed by co-evaporation with toluene (×3) and the residue purified via silica gel chromatography (ethyl acetate dichloromethane/methanol 4:1).

Workup

  1. customThe reaction mixture was evaporated down
  2. customthe residue purified via silica gel chromatography (ethyl acetate dichloromethane/methanol 4:1)

Sources & evidence

ORD record
ord-20cf3d145d7945e985bad865fd30c64b
Source dataset
uspto-grants-2015_11
Patent number
US09187478B2

Reaction notes

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