Tetrahydrofuran → 3-Amino-5-(4-chlorophenyl)-6-(2,4-dichlorophenyl)furo[2,3-b]-pyridine-2-carbonitrile

HRID 8797ノート

反応式

HRID 8797 の反応式
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:9]([C:20]3[CH:25]=[CH:24][C:23]([Cl:26])=[CH:22][C:21]=3[Cl:27])=[N:10][C:11]([O:16][CH2:17][C:18]#[N:19])=[C:12]([CH:15]=2)[C:13]#[N:14])=[CH:4][CH:3]=1.C[Si]([N-][Si](C)(C)C)(C)C.[Li+].C1COCC1>>[NH2:14][C:13]1[C:12]2[C:11](=[N:10][C:9]([C:20]3[CH:25]=[CH:24][C:23]([Cl:26])=[CH:22][C:21]=3[Cl:27])=[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]#[N:19]

参加物

4

反応物 3

HCID 8028TetrahydrofuranHCID 2733832Lithium HexamethyldisilazideHCID 21984888HCID 21984888、化合物

生成物 1

HCID 103196423-Amino-5-(4-chlorophenyl)-6-(2,4-dichlorophenyl)furo[2,3-b]-pyridine-2-carbonitrile

反応条件

温度
0 °C

実験手順

A solution of the product from Step A (0.132 g; 0.319 mmol) in TB (3 mL) cooled to 0° C. was treated with 1 M solution of lithium bis(trimethylsilyl)amide in THF (701 μL; 0.701 mmol) and stirred at 0° C. under nitrogen for 15 minutes. The reaction mixture was warmed to room temperature and then stirred for an additional 15 minutes. The reaction mixture was partitioned between EtOAc and 10% NaHSO4 aqueous 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 30% ethyl acetate-hexane gradient) gave the title compound. HPLC/MS: 413.9 (M+1), 415.9 (M+3); Rt=4.50 min.

後処理

  1. temperatureThe reaction mixture was warmed to room temperature
  2. stirringstirred for an additional 15 minutes
  3. customThe reaction mixture was partitioned between EtOAc and 10% NaHSO4 aqueous 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 30% ethyl acetate-hexane gradient)

出典と根拠

ORDレコード
ord-b22fb182a5a04572853f4b28447fe852
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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