2-Aminopyridine → 669091-15-0

HRID 2213092Notes

Reaction equation

HRID 2213092 reaction equation
Br[CH2:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][N:12]=2)=[C:7]([O:17][CH3:18])[CH:6]=1)=O.[NH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][N:21]=1>C(O)C>[CH3:18][O:17][C:7]1[CH:6]=[C:5]([C:3]2[N:19]=[C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][N:21]3[CH:2]=2)[CH:10]=[CH:9][C:8]=1[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][N:12]=1

Participants

4

Reactant 2

HCID 104392-AminopyridineHCID 219565182-Bromo-1-[3-methoxy-4-(pyridin-2-yl)phenyl]ethan-1-one

Product 1

HCID 10380127669091-15-0

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 2-bromo-1-(3-methoxy-4-pyridin-2-ylphenyl)ethanone (130 mg, 0.42 mmol) in ethanol (5 mL) was added 2-aminopyridine (40 mg, 0.42 mmol). The resulting reaction mixture was heated to reflux for 2 h and concentrated. The residue was dissolved in CH2Cl2 (20 mL) and washed with a solution of saturated aqueous NaHCO3 (3×10 mL), dried (MgSO4) and concentrated. The residue was purified by flash column chromatography on silica gel eluting with EtOAc:hexanes (1:1 to 1:0) to afford 2-(3-methoxy-4-pyridin-2-ylphenyl)imidazo[1,2-a]pyridine as a yellow solid. 1H NMR (CDCl3, 300 MHz) δ 8.72 (d, 1H), 8.13 (d, 1H), 7.75 (s, 1H), 7.91 (d, 1H), 7.87 (d, 1H), 7.75 (s, 1H), 7.70 (dd, 1H), 7.66 (d, 1H), 7.57 (dd, 1H), 7.20 (m, 2H), 6.79 (dd, 1H), 4.00 (s, 3H) ppm. MS (ESI) 302 (M)+.

Workup

  1. customThe resulting reaction mixture
  2. temperaturewas heated
  3. temperatureto reflux for 2 h
  4. concentrationconcentrated
  5. dissolutionThe residue was dissolved in CH2Cl2 (20 mL)
  6. washwashed with a solution of saturated aqueous NaHCO3 (3×10 mL)
  7. dry with materialdried (MgSO4)
  8. concentrationconcentrated
  9. customThe residue was purified by flash column chromatography on silica gel eluting with EtOAc:hexanes (1:1 to 1:0)

Sources & evidence

ORD record
ord-a20fb6a6b069406dbfa230b52dd61ca2
Source dataset
uspto-grants-2006_09
Patent number
US07105533B2

Reaction notes

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