Picolinic acid → HCID 118114085, compound

HRID 1509654Notes

Reaction equation

HRID 1509654 reaction equation
Br[C:2]1[CH:3]=[C:4]([N:12]2[CH:16]=[CH:15][N:14]=[CH:13]2)[CH:5]=[C:6]([C:8]([CH3:11])([CH3:10])[CH3:9])[CH:7]=1.[C:17]([C:21]1[CH:26]=[CH:25][N:24]=[C:23]([N:27]2[C:39]3[CH:38]=[C:37]([OH:40])[CH:36]=[CH:35][C:34]=3[C:33]3[C:28]2=[CH:29][CH:30]=[CH:31][CH:32]=3)[CH:22]=1)([CH3:20])([CH3:19])[CH3:18].N1C=CC=CC=1C(O)=O.[O-]P([O-])([O-])=O.[K+].[K+].[K+]>CS(C)=O.[Cu]I>[C:8]([C:6]1[CH:7]=[C:2]([CH:3]=[C:4]([N:12]2[CH:16]=[CH:15][N:14]=[CH:13]2)[CH:5]=1)[O:40][C:37]1[CH:36]=[CH:35][C:34]2[C:33]3[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=3)[N:27]([C:23]3[CH:22]=[C:21]([C:17]([CH3:20])([CH3:19])[CH3:18])[CH:26]=[CH:25][N:24]=3)[C:39]=2[CH:38]=1)([CH3:11])([CH3:10])[CH3:9]

Participants

7

Reactant 4

HCID 1018Picolinic acidHCID 62657Potassium Phosphate, TribasicHCID 1181139559-(4-(tert-Butyl)pyridin-2-yl)-9H-carbazol-2-olHCID 118114109HCID 118114109, compound

Product 1

HCID 118114085HCID 118114085, compoundYield 81%

Reagents, catalysts & solvents 2

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

Conditions

Temperature
100 °C

Procedure

A mixture of 1-(3-bromo-5-tert-butylphenyl)-1H-imidazole 7 (0.98 g, 3.50 mmol, 1.0 eq), 9-(4-tert-butylpyridin-2-yl)-9H-carbazol-2-ol 10 (1.11 g, 3.50 mmol, 1.0 eq), CuI (0.10 g, 0.53 mmol, 0.15 eq), picolinic acid (0.13 g, 1.05 mmol, 0.30 eq) and K3PO4 (1.78 g, 8.40 mmol, 2.4 eq) in DMSO (7 mL) was stirred at a temperature of 100° C. for four days under a nitrogen atmosphere, then cooled to ambient temperature. The solid was filtered off and washed with plenty of ethyl acetate. The filtrate was washed with water three times and then dried over sodium sulfate and filtered. The filtrate was concentrated under reduced pressure and the residue was purified through column chromatography on silica gel using hexane/ethyl acetate as an eluent to obtain the desired product as a brown sticky liquid (1.45 g in 81% yield).

Workup

  1. temperaturecooled to ambient temperature
  2. filtrationThe solid was filtered off
  3. washwashed with plenty of ethyl acetate
  4. washThe filtrate was washed with water three times
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. concentrationThe filtrate was concentrated under reduced pressure
  8. customthe residue was purified through column chromatography on silica gel

Sources & evidence

ORD record
ord-866b4dd9660447f483b5df857d09b08c
Source dataset
uspto-grants-2015_12
Patent number
US09224963B2

Reaction notes

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