Azidotrimethylsilane → (Z)-4-azido-1,3-dihydro-5-nitro-3-[(1H-pyrrol-2-yl)methylene]-2H-indol-2-one

HRID 1859066노트

반응식

HRID 1859066 반응식
F[C:2]1[C:10]([N+:11]([O-:13])=[O:12])=[CH:9][CH:8]=[C:7]2[C:3]=1/[C:4](=[CH:15]/[C:16]1[NH:17][CH:18]=[CH:19][CH:20]=1)/[C:5](=[O:14])[NH:6]2.CCN(C(C)C)C(C)C.C[Si]([N:34]=[N+:35]=[N-:36])(C)C>C1COCC1.CCO>[N:34]([C:2]1[C:10]([N+:11]([O-:13])=[O:12])=[CH:9][CH:8]=[C:7]2[C:3]=1/[C:4](=[CH:15]/[C:16]1[NH:17][CH:18]=[CH:19][CH:20]=1)/[C:5](=[O:14])[NH:6]2)=[N+:35]=[N-:36]

참가 물질

5

반응물 3

HCID 78378AzidotrimethylsilaneHCID 81531DiisopropylethylamineHCID 21253427(Z)-1,3-Dihydro-4-fluoro-5-nitro-3-[(1H-pyrrol-2-yl)methylene]-2H-indol-2-one

생성물 1

HCID 21253446(Z)-4-azido-1,3-dihydro-5-nitro-3-[(1H-pyrrol-2-yl)methylene]-2H-indol-2-one수율 79%

시약·촉매·용매 1

HCID 21873804Tetrahydrofuran ethanol용매

실험 절차

(Z)-1,3-Dihydro4-fluoro-5-nitro-3-[(1H-pyrrol-2-yl)methylene]-2H-indol-2-one (400 mg, 1.46 mmol) (from Example 10) was suspended in THF/EtOH (20 mL/10 mL). Hunig's base (diisopropylethyl amine, 3.8 mL, 22 mmol)(Aldrich) and trimethylsilyl azide (1.87 mL, 14.65 mmol)(Aldrich) were successively added at r.t. The mixture was refluxed for 12 h. The homogeneous reaction mixture was cooled to r.t. and quenched with 1N HCl. The precipitate was collected by suction filtration, washed with water and dried in a vacuum oven to yield (Z)-4-azido-1,3-dihydro-5-nitro-3-[(1H-pyrrol-2-yl)methylene]-2H-indol-2-one as a red solid (Yield 340 mg, 79%).

후처리

  1. temperatureThe mixture was refluxed for 12 h
  2. customquenched with 1N HCl
  3. filtrationThe precipitate was collected by suction filtration
  4. washwashed with water
  5. customdried in a vacuum oven

출처 및 근거

ORD 기록
ord-86fc87801c9f47e48690f77207374ad8
출처 데이터셋
uspto-grants-2000_11
특허 번호
US06153634

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