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

HRID 8783노트

반응식

HRID 8783 반응식
[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]

참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-7e87674c3aba466295873e89f7a3ec9d
출처 데이터셋
uspto-grants-2006_08
특허 번호
US07091216B2

반응 노트

불러오는 중…