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

HRID 1859066
Notes
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Reaction equation

HRID 1859066 reaction equation
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]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 21873804
Tetrahydrofuran ethanol
Solvent

Procedure

(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%).

Workup

  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

Sources & evidence

ORD record
ord-86fc87801c9f47e48690f77207374ad8
Source dataset
uspto-grants-2000_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06153634

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes