Potassium Carbonate → 2-[4-(5-Pyridin-4-yl-pyrazol-1-yl)-phenoxymethyl]-quinoline

HRID 33875

Reaction equation

HRID 33875 reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([C:7]2[N:11]([C:12]3[CH:17]=[CH:16][C:15]([OH:18])=[CH:14][CH:13]=3)[N:10]=[CH:9][CH:8]=2)=[CH:3][CH:2]=1.C(=O)([O-])[O-].[K+].[K+].Cl[CH2:26][C:27]1[CH:36]=[CH:35][C:34]2[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=2)[N:28]=1>CC(C)=O.[Cl-].[Na+].O>[N:1]1[CH:2]=[CH:3][C:4]([C:7]2[N:11]([C:12]3[CH:17]=[CH:16][C:15]([O:18][CH2:26][C:27]4[CH:36]=[CH:35][C:34]5[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=5)[N:28]=4)=[CH:14][CH:13]=3)[N:10]=[CH:9][CH:8]=2)=[CH:5][CH:6]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 203942-(Chloromethyl)quinolineHCID 685764624-(5-Pyridin-4-yl-pyrazol-1-yl)-phenol

Product 1

HCID 116608572-[4-(5-Pyridin-4-yl-pyrazol-1-yl)-phenoxymethyl]-quinolineYield 69.6%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 57417360Sodium chloride; waterSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of 4-(5-Pyridin-4-yl-pyrazol-1-yl)-phenol (82 mg) in acetone was added potassium carbonate (153 mg) and 2-Chloromethyl-quinoline (95 mg) and the reaction mixture heated at 60° C. for 18 h. The reaction mixture was poured into brine and extracted with ethyl acetate, dried magnesium sulfate, filtered and concentrated. Purification via combiflash MPLC provided the title compound (91 mg). 1H NMR (400 MHz, CDCl3) δ 8.51 (m, 2 H), 8.20 (d, J=8.7 Hz, 1 H), 8.06 (d, J=8.7 Hz, 1 H), 7.83 (d, J=7.1 Hz, 1H), 7.74 (m, 2H), 7.65 (d, J=8.7 Hz, 1 H), 7.57 (m, 1H), 7.20 (d, J=8.7 Hz, 2 H), 7.09 (d, J=5.8 Hz, 2H), 7.02 (d, J=9.1 Hz, 2H), 6.60 (d, J=1.7 Hz, 1H), 5.39 (s, 2H); MS: (M+H m/z=379.0).

Workup

  1. extractionextracted with ethyl acetate, dried magnesium sulfate
  2. filtrationfiltered
  3. concentrationconcentrated
  4. customPurification via combiflash MPLC

Sources & evidence

ORD record
ord-b53715596bbe47cb877f1ff216902a5e
Source dataset
uspto-grants-2008_09
Patent number
US07429665B2

Linked notes

Loading…