Picolinic acid → HCID 66748025, compound

HRID 1622793Notes

Reaction equation

HRID 1622793 reaction equation
P([O-])([O-])([O-])=O.[K+].[K+].[K+].N1C=CC=CC=1C(O)=O.[NH2:18][C:19]1[C:24]([C:25]2[CH:30]=[CH:29][C:28]([OH:31])=[CH:27][CH:26]=2)=[CH:23][CH:22]=[CH:21][N:20]=1.I[C:33]1[CH:38]=[CH:37][CH:36]=[C:35]([C:39]([F:42])([F:41])[F:40])[CH:34]=1>CS(C)=O.[Cu]I>[F:40][C:39]([F:42])([F:41])[C:35]1[CH:34]=[C:33]([CH:38]=[CH:37][CH:36]=1)[O:31][C:28]1[CH:29]=[CH:30][C:25]([C:24]2[C:19]([NH2:18])=[N:20][CH:21]=[CH:22][CH:23]=2)=[CH:26][CH:27]=1

Participants

7

Reactant 4

HCID 1018Picolinic acidHCID 62657Potassium Phosphate, TribasicHCID 67868Benzene, 1-iodo-3-(trifluoromethyl)-HCID 667484774-(2-Aminopyridin-3-yl)phenol

Product 1

HCID 66748025HCID 66748025, compoundYield 65.4%

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
120 °C

Procedure

Copper(I) iodide (61.4 mg) was added to a mixture of tripotassium phosphate (1026 mg), picolinic acid (39.7 mg), 4-(2-aminopyridin-3-yl)phenol (300 mg) and 1-iodo-3-(trifluoromethyl)benzene (526 mg) in DMSO (6 mL). The mixture was stirred at 120° C. under nitrogen for 2 hr. The mixture was purified by column chromatography (silica gel, eluted with EtOAc in hexane) to give the title compound (348 mg) as a pale yellow solid.

Workup

  1. customThe mixture was purified by column chromatography (silica gel, eluted with EtOAc in hexane)

Sources & evidence

ORD record
ord-c0f13f666cef4c6081aa88eb2473d3c1
Source dataset
uspto-grants-2014_07
Patent number
US08778934B2

Reaction notes

Loading…