Picolinic acid → HCID 70654361, compound

HRID 539452Notes

Reaction equation

HRID 539452 reaction equation
[CH:1]([C:4]1[CH:5]=[C:6]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[CH:7]=[C:8]([CH:22]([CH3:24])[CH3:23])[C:9]=1[N:10]1[CH:14]=[CH:13][N:12]=[C:11]1[C:15]1[CH:16]=[C:17]([OH:21])[CH:18]=[CH:19][CH:20]=1)([CH3:3])[CH3:2].[CH:31]([C:34]1[CH:35]=[C:36]([C:55]2[CH:60]=[CH:59][CH:58]=[CH:57][CH:56]=2)[CH:37]=[C:38]([CH:52]([CH3:54])[CH3:53])[C:39]=1[N:40]1[CH:44]=[CH:43][N:42]=[C:41]1[C:45]1[CH:50]=[CH:49][CH:48]=[C:47](I)[CH:46]=1)([CH3:33])[CH3:32].N1C=CC=CC=1C(O)=O.P([O-])([O-])([O-])=O.[K+].[K+].[K+]>CS(C)=O.O.[Cu]I.CC#N>[O:21]([C:49]1[CH:50]=[C:45]([C:41]2[N:40]([C:39]3[C:38]([CH:52]([CH3:54])[CH3:53])=[CH:37][C:36]([C:55]4[CH:60]=[CH:59][CH:58]=[CH:57][CH:56]=4)=[CH:35][C:34]=3[CH:31]([CH3:33])[CH3:32])[CH:44]=[CH:43][N:42]=2)[CH:46]=[CH:47][CH:48]=1)[C:17]1[CH:16]=[C:15]([C:11]2[N:10]([C:9]3[C:4]([CH:1]([CH3:2])[CH3:3])=[CH:5][C:6]([C:25]4[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=4)=[CH:7][C:8]=3[CH:22]([CH3:24])[CH3:23])[CH:14]=[CH:13][N:12]=2)[CH:20]=[CH:19][CH:18]=1

Participants

9

Reactant 4

HCID 1018Picolinic acidHCID 62657Potassium Phosphate, TribasicHCID 70654380HCID 70654380, compoundHCID 70654670HCID 70654670, compound

Product 1

HCID 70654361HCID 70654361, compoundYield 70%

Reagents, catalysts & solvents 4

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 679Dimethyl SulfoxideSolventHCID 962WaterSolventHCID 6342AcetonitrileSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 3-(1-(3,5-diisopropyl-[1,1′-biphenyl]-4-yl)-1H-imidazol-2-yl)phenol (3.12 g, 7.87 mmol), 1-(3,5-diisopropyl-[1,1′-biphenyl]-4-yl)-2-(3-iodophenyl)-1H-imidazole (3.98 g, 7.87 mmol), copper(I) iodide (0.15 g, 0.787 mmol), picolinic acid (2.91 g, 23.61 mmol) and potassium phosphate (8.35 g, 39.3 mmol) in DMSO (45 mL) was heated at 100° C. under a nitrogen atmosphere. The reaction progress was monitored by HPLC (C18, 95% MeCN in water, 1.0 mL per min.). HPLC after 4 days indicated about 70% desired product. The reaction was worked up until no increase of desired product. 5% aqueous sodium carbonate was added to the reaction mixture until pH around 10. The resulting solid was isolated by filtration and washed with water (3×). This crude mixture was purified by aluminum column chromatography (eluants: DCM/MeOH: 99/1 to 9/5), followed by silica gel column chromatography (eluant: Hexane/acetone: 7/3) to afford a light yellow solid (3.6 g, 59% yield).

Sources & evidence

ORD record
ord-af2bf8afcb3c4825b87dd2261ce5cf2a
Source dataset
uspto-grants-2014_10
Patent number
US08871361B2

Reaction notes

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