Cesium carbonate → 2-(4-(3-(2-Methylpyridin-4-YL)pyridin-2-yloxy)benzyl)-1H-benzo[D]imidazole

HRID 1880032Notes

Reaction equation

HRID 1880032 reaction equation
F[C:2]1[C:7]([C:8]2[CH:13]=[CH:12][N:11]=[C:10]([CH3:14])[CH:9]=2)=[CH:6][CH:5]=[CH:4][N:3]=1.[NH:15]1[C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][C:18]=2[N:17]=[C:16]1[CH2:24][C:25]1[CH:30]=[CH:29][C:28]([OH:31])=[CH:27][CH:26]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>O>[CH3:14][C:10]1[CH:9]=[C:8]([C:7]2[C:2]([O:31][C:28]3[CH:29]=[CH:30][C:25]([CH2:24][C:16]4[NH:15][C:19]5[CH:20]=[CH:21][CH:22]=[CH:23][C:18]=5[N:17]=4)=[CH:26][CH:27]=3)=[N:3][CH:4]=[CH:5][CH:6]=2)[CH:13]=[CH:12][N:11]=1

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 3939864-((1H-Benzo[D]imidazol-2-YL)methyl)phenolHCID 585485722-Fluoro-3-(2-methylpyridin-4-yl)pyridine

Product 1

HCID 462162262-(4-(3-(2-Methylpyridin-4-YL)pyridin-2-yloxy)benzyl)-1H-benzo[D]imidazole

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 2-fluoro-3-(2-methylpyridin-4-yl)pyridine (1.00 g, 5.31 mmol), 4-((1H-benzo[d]imidazol-2-yl)methyl)phenol (1.43 g, 6.38 mmol) and cesium carbonate (2.60 g, 7.97 mmol) was heated to 80° C. for 16 h. After cooling to room temperature, the mixture was diluted with H2O and extracted with 25% i-PrOH/CHCl3 (3×). The combined organics were dried over Na2SO4, filtered and concentrated. The residue was purified using column chromatography (Acetone/Hexanes=0→80%) to give the title compound. MS (ESI, pos. ion) m/z: 393 (M+1). IC50 (uM) ++++.

Workup

  1. temperatureAfter cooling to room temperature
  2. extractionextracted with 25% i-PrOH/CHCl3 (3×)
  3. dry with materialThe combined organics were dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was purified

Sources & evidence

ORD record
ord-947703cbabcb40778680bea9ad89d757
Source dataset
uspto-grants-2012_11
Patent number
US08318718B2

Reaction notes

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