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

HRID 8797노트

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HRID 8797 반응식
[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]

참가 물질

4

반응물 3

HCID 8028TetrahydrofuranHCID 2733832Lithium HexamethyldisilazideHCID 21984888HCID 21984888, 화합물

생성물 1

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

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온도
0 °C

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-b22fb182a5a04572853f4b28447fe852
출처 데이터셋
uspto-grants-2006_08
특허 번호
US07091216B2

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