8-Hydroxyquinoline → HCID 24985793, compound

HRID 1887324Notes

Reaction equation

HRID 1887324 reaction equation
Br[C:2]1[S:3][C:4]([C:8]([O:10][CH2:11][CH3:12])=[O:9])=[C:5]([CH3:7])[N:6]=1.[C:13]1([C:19]2[CH:24]=[CH:23][N:22]=[C:21]([OH:25])[CH:20]=2)[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.OC1C=CC=C2C=1N=CC=C2.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O.[Cu]I>[CH3:7][C:5]1[N:6]=[C:2]([N:22]2[CH:23]=[CH:24][C:19]([C:13]3[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=3)=[CH:20][C:21]2=[O:25])[S:3][C:4]=1[C:8]([O:10][CH2:11][CH3:12])=[O:9]

Participants

7

Reactant 4

HCID 19238-HydroxyquinolineHCID 11430Potassium CarbonateHCID 5987864-Phenylpyridin-2-olHCID 2824057Ethyl 2-bromo-4-methyl-1,3-thiazole-5-carboxylate

Product 1

HCID 24985793HCID 24985793, compoundYield 73.4%

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of ethyl 2-bromo-4-methylthiazole-5-carboxylate (0.50 g, 2.00 mmol) in anhydrous N,N-dimethylformamide (10 mL) was added 4-phenylpyridin-2-ol (0.31 g, 1.80 mmol), copper(I) iodide (0.053 g, 0.28 mmol), 8-hydroxyquinoline (0.041 g, 0.28 mmol), and potassium carbonate (0.39 g, 2.80 mmol). The mixture was degassed and the flask was filled with nitrogen. The reaction mixture was heated at 100° C. for 6 hours and then diluted with ethyl acetate (25 mL), washed with 14% aqueous ammonium hydroxide (2×7 mL) and brine (7 mL). The organic layer was dried over anhydrous sodium sulfate, filtered concentrated in vacuo to afford as a yellowish solid (0.45 g, 66%): 1H NMR (300 MHz, DMSO-d6) δ 8.83-8.75 (m, 1H), 7.88-7.81 (m, 2H), 7.60-7.50 (m, 3H), 7.14-7.03 (m, 2H), 4.26 (q, J=7.0 Hz, 2H), 2.64 (s, 3H), 1.28 (t, J=7.0 Hz, 3H); MS (ES+) m/z 341.6 (M+1).

Workup

  1. customThe mixture was degassed
  2. additionthe flask was filled with nitrogen
  3. additiondiluted with ethyl acetate (25 mL)
  4. washwashed with 14% aqueous ammonium hydroxide (2×7 mL) and brine (7 mL)
  5. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-208c879e9e154b1d8522f8361ec92cfd
Source dataset
uspto-grants-2013_08
Patent number
US08501746B2

Reaction notes

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