Water → HCID 9857533, compound

HRID 985506Notes

Reaction equation

HRID 985506 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][N:5]2[C:8]([C:11]3[CH:12]=[C:13]([OH:17])[CH:14]=[CH:15][CH:16]=3)=[CH:9][N:10]=[C:4]2[CH:3]=1.[H-].[Na+].Br[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][N:22]=1.O>CN(C)C=O>[CH3:1][C:2]1[CH:7]=[CH:6][N:5]2[C:8]([C:11]3[CH:16]=[CH:15][CH:14]=[C:13]([O:17][C:21]4[CH:26]=[CH:25][CH:24]=[CH:23][N:22]=4)[CH:12]=3)=[CH:9][N:10]=[C:4]2[CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 79732-BromopyridineHCID 24758Sodium hydrideHCID 11644260HCID 11644260, compound

Product 1

HCID 9857533HCID 9857533, compoundYield 24%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

3-(7-Methylimidazo[1,2-α]pyridin-3-yl)phenol (310 mg, 1.4 mmol) in anhydrous N,N-dimethylformamide (5 ml) was treated with sodium hydride (60% dispersion in mineral oil, 70 mg, 1.75 mmol) and then stirred at ambient temperature for 30 minutes. 2-Bromopyridine (0.16 ml, 1.67 mmol) was added and the reaction mixture heated at 120° C. for 4 days, poured into water (25 ml) and extracted with ethyl acetate (2×30 ml). The combined organic phases were washed with water (3×20 ml), dried over anhydrous magnesium sulphate and concentrated in vacuo. Purification by preparative TLC gave the title compound as a colourless oil (100 mg, 24%). 1H NMR (400 MHz, CDCl3) δH 2.64 (3H, s), 7.08-7.10 (1H, m), 7.14-7.17 (1H, m), 7.33-7.37 (2H, m), 7.50-7.55 (2H, m), 7.66-7.70 (1H, m), 7.78 (1H, s), 7.85-7.90 (1H, m), 8.07 (1H, s), 8.15-8.16 (1H, m), 8.65 (1H, d, J 7); m/z (ES+) 302 (M++H).

Workup

  1. temperaturethe reaction mixture heated at 120° C. for 4 days
  2. extractionextracted with ethyl acetate (2×30 ml)
  3. washThe combined organic phases were washed with water (3×20 ml)
  4. dry with materialdried over anhydrous magnesium sulphate
  5. concentrationconcentrated in vacuo
  6. customPurification by preparative TLC

Sources & evidence

ORD record
ord-88e76cc1ac704296b4785c755ba549e2
Source dataset
uspto-grants-2005_03
Patent number
US06872731B2

Reaction notes

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