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

HRID 1531152ノート

反応式

HRID 1531152 の反応式
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]

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 21873804Tetrahydrofuran ethanol溶媒

実験手順

(Z)-1,3-Dihydro-4-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%).

後処理

  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

出典と根拠

ORDレコード
ord-53187e2a0ace47b0989eb8a689653988
出典データセット
uspto-grants-2001_03
特許番号
US06197804B1

反応ノート

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