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

HRID 8783ノート

反応式

HRID 8783 の反応式
[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]

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-7e87674c3aba466295873e89f7a3ec9d
出典データセット
uspto-grants-2006_08
特許番号
US07091216B2

反応ノート

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