Sodium ethoxide → 1-(3-Amino-5-(4-chlorophenyl)-6-(2,4-dichlorophenyl)furo[2,3-b]pyridin-2-yl)ethanone

HRID 8783Notes

Reaction equation

HRID 8783 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:9]([C:21]3[CH:26]=[CH:25][C:24]([Cl:27])=[CH:23][C:22]=3[Cl:28])=[N:10][C:11]([O:16][CH2:17][C:18](=[O:20])[CH3:19])=[C:12]([CH:15]=2)[C:13]#[N:14])=[CH:4][CH:3]=1.[O-]CC.[Na+]>C(O)C>[NH2:14][C:13]1[C:12]2[C:11](=[N:10][C:9]([C:21]3[CH:26]=[CH:25][C:24]([Cl:27])=[CH:23][C:22]=3[Cl:28])=[C:8]([C:5]3[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=3)[CH:15]=2)[O:16][C:17]=1[C:18](=[O:20])[CH3:19]

Participants

4

Reactant 2

HCID 2723922Sodium ethoxideHCID 219849455-(4-Chlorophenyl)-6-(2,4-dichlorophenyl)-2-(2-oxopropoxy)-nicotinonitrile

Product 1

HCID 104105121-(3-Amino-5-(4-chlorophenyl)-6-(2,4-dichlorophenyl)furo[2,3-b]pyridin-2-yl)ethanone

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of the product from Step A (0.126 g; 0.292 mmol) in ethanol (4 mL) was treated with sodium ethoxide (0.040 g; 0.584 mmol) and stirred at reflux for 1 hour. The reaction was allowed to cool to room temperature and quenched with saturated NaHCO3 solution. The reaction mixture was partitioned between ethyl acetate and saturated NaHCO3 solution. The organic layer was washed twice with saturated NaHCO3 solution, brine, dried (Na2SO4), filtered, and concentrated in vacuo. Purification by MPLC (silica gel; 0% to 20% ethyl acetate-hexane gradient) gave the title compound. HPLC/MS: 430.9 (M+1), 432.9 (M+3); Rt=4.04 min.

Workup

  1. temperatureat reflux for 1 hour
  2. customquenched with saturated NaHCO3 solution
  3. customThe reaction mixture was partitioned between ethyl acetate and saturated NaHCO3 solution
  4. washThe organic layer was washed twice with saturated NaHCO3 solution, brine
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customPurification by MPLC (silica gel; 0% to 20% ethyl acetate-hexane gradient)

Sources & evidence

ORD record
ord-7e87674c3aba466295873e89f7a3ec9d
Source dataset
uspto-grants-2006_08
Patent number
US07091216B2

Reaction notes

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