Picolinic acid → HCID 66748403, compound

HRID 1622761Notes

Reaction equation

HRID 1622761 reaction equation
N1C=CC=CC=1C(O)=O.[NH2:10][C:11]1[C:16]([C:17]2[CH:22]=[CH:21][C:20]([OH:23])=[CH:19][CH:18]=2)=[CH:15][C:14]([CH3:24])=[CH:13][N:12]=1.P([O-])([O-])([O-])=O.[K+].[K+].[K+].Br[C:34]1[CH:39]=[CH:38][C:37]([F:40])=[C:36]([O:41][CH3:42])[CH:35]=1>[Cu]I.CS(C)=O>[F:40][C:37]1[CH:38]=[CH:39][C:34]([O:23][C:20]2[CH:19]=[CH:18][C:17]([C:16]3[C:11]([NH2:10])=[N:12][CH:13]=[C:14]([CH3:24])[CH:15]=3)=[CH:22][CH:21]=2)=[CH:35][C:36]=1[O:41][CH3:42]

Participants

7

Reactant 4

HCID 1018Picolinic acidHCID 62657Potassium Phosphate, TribasicHCID 136049094-Bromo-1-fluoro-2-methoxybenzeneHCID 50953296HCID 50953296, compound

Product 1

HCID 66748403HCID 66748403, compoundYield 44.6%

Reagents, catalysts & solvents 2

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

Conditions

Temperature
130 °C

Procedure

Copper(I) iodide (95 mg) was added to a mixture of picolinic acid (61.5 mg), 4-(2-amino-5-methylpyridin-3-yl)phenol (500 mg), tripotassium phosphate (1590 mg), 4-bromo-1-fluoro-2-methoxybenzene (614 mg) and DMSO (8 mL). The mixture was stirred at 130° C. under nitrogen for 10 hr. The insoluble solid was removed by filtration through silica gel/Celite pad (eluted with EtOAc). Silica-gel was added to the filtrate and the volatiles were removed in vacuo. The mixture supported on silica-gel was purified by column chromatography (NH-silica gel, eluted with EtOAc in hexane) to give the title compound (361 mg) as pale yellow oil.

Workup

  1. customThe insoluble solid was removed by filtration through silica gel/Celite pad (eluted with EtOAc)
  2. additionSilica-gel was added to the filtrate
  3. customthe volatiles were removed in vacuo
  4. customwas purified by column chromatography (NH-silica gel, eluted with EtOAc in hexane)

Sources & evidence

ORD record
ord-fed440e0958f427dae091c7f21418768
Source dataset
uspto-grants-2014_07
Patent number
US08778934B2

Reaction notes

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